JP6940481B2 - 四座配位子、その製造方法及び合成中間体並びにその遷移金属錯体 - Google Patents
四座配位子、その製造方法及び合成中間体並びにその遷移金属錯体 Download PDFInfo
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- JP6940481B2 JP6940481B2 JP2018509478A JP2018509478A JP6940481B2 JP 6940481 B2 JP6940481 B2 JP 6940481B2 JP 2018509478 A JP2018509478 A JP 2018509478A JP 2018509478 A JP2018509478 A JP 2018509478A JP 6940481 B2 JP6940481 B2 JP 6940481B2
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- 229910052723 transition metal Inorganic materials 0.000 title claims description 50
- 150000003624 transition metals Chemical class 0.000 title claims description 50
- 239000003446 ligand Substances 0.000 title claims description 49
- 238000004519 manufacturing process Methods 0.000 title claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 168
- 229910052717 sulfur Inorganic materials 0.000 claims description 64
- 229910052757 nitrogen Inorganic materials 0.000 claims description 56
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 229910052751 metal Inorganic materials 0.000 claims description 19
- 239000002184 metal Substances 0.000 claims description 18
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000004437 phosphorous atom Chemical group 0.000 claims description 11
- 229910000085 borane Inorganic materials 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 7
- 239000013543 active substance Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 150000004696 coordination complex Chemical class 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 description 117
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 113
- -1 halogenated alcohols Chemical class 0.000 description 92
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
- 230000005291 magnetic effect Effects 0.000 description 65
- 238000005481 NMR spectroscopy Methods 0.000 description 61
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 58
- 238000002955 isolation Methods 0.000 description 55
- 239000000243 solution Substances 0.000 description 54
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 51
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 51
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 47
- 238000003786 synthesis reaction Methods 0.000 description 41
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- 239000000203 mixture Substances 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 31
- 238000011282 treatment Methods 0.000 description 31
- 239000000725 suspension Substances 0.000 description 30
- 230000015572 biosynthetic process Effects 0.000 description 29
- 238000000746 purification Methods 0.000 description 29
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- 238000002360 preparation method Methods 0.000 description 28
- 238000001816 cooling Methods 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 26
- 238000004817 gas chromatography Methods 0.000 description 25
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 25
- 239000000843 powder Substances 0.000 description 22
- 238000010992 reflux Methods 0.000 description 22
- 239000003054 catalyst Substances 0.000 description 21
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 21
- 239000000543 intermediate Substances 0.000 description 20
- 238000005984 hydrogenation reaction Methods 0.000 description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 18
- 235000019445 benzyl alcohol Nutrition 0.000 description 17
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 16
- 239000002585 base Substances 0.000 description 16
- 230000003197 catalytic effect Effects 0.000 description 16
- 239000013078 crystal Substances 0.000 description 16
- 150000002148 esters Chemical class 0.000 description 16
- 239000010410 layer Substances 0.000 description 16
- 238000005259 measurement Methods 0.000 description 16
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 15
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 15
- 239000003480 eluent Substances 0.000 description 15
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 229910052739 hydrogen Inorganic materials 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- REGBTJYLCZYZPV-UHFFFAOYSA-N 2-fluorobenzenethiol Chemical compound FC1=CC=CC=C1S.FC1=CC=CC=C1S REGBTJYLCZYZPV-UHFFFAOYSA-N 0.000 description 12
- 238000010898 silica gel chromatography Methods 0.000 description 12
- 150000003623 transition metal compounds Chemical class 0.000 description 12
- 230000014759 maintenance of location Effects 0.000 description 11
- 238000000967 suction filtration Methods 0.000 description 11
- 239000012327 Ruthenium complex Substances 0.000 description 10
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 10
- 239000002002 slurry Substances 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 9
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- 150000004687 hexahydrates Chemical class 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 239000005457 ice water Substances 0.000 description 9
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 229910052744 lithium Inorganic materials 0.000 description 8
- 229940095102 methyl benzoate Drugs 0.000 description 8
- 150000007944 thiolates Chemical class 0.000 description 8
- LAXRNWSASWOFOT-UHFFFAOYSA-J (cymene)ruthenium dichloride dimer Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Ru+2].[Ru+2].CC(C)C1=CC=C(C)C=C1.CC(C)C1=CC=C(C)C=C1 LAXRNWSASWOFOT-UHFFFAOYSA-J 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 229910052783 alkali metal Chemical group 0.000 description 7
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 7
- 239000012535 impurity Substances 0.000 description 7
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 7
- 150000003573 thiols Chemical class 0.000 description 7
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 6
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 150000002825 nitriles Chemical class 0.000 description 6
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 6
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical class [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 229910001220 stainless steel Inorganic materials 0.000 description 6
- 239000010935 stainless steel Substances 0.000 description 6
- KGKAYWMGPDWLQZ-UHFFFAOYSA-N 1,2-bis(bromomethyl)benzene Chemical group BrCC1=CC=CC=C1CBr KGKAYWMGPDWLQZ-UHFFFAOYSA-N 0.000 description 5
- JSGVZVOGOQILFM-UHFFFAOYSA-N 3-methoxy-1-butanol Chemical compound COC(C)CCO JSGVZVOGOQILFM-UHFFFAOYSA-N 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 229910010277 boron hydride Inorganic materials 0.000 description 5
- 150000004683 dihydrates Chemical class 0.000 description 5
- 150000002506 iron compounds Chemical class 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 150000002596 lactones Chemical class 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 150000003138 primary alcohols Chemical class 0.000 description 5
- 150000003304 ruthenium compounds Chemical class 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N 2,2-dimethylbutane Chemical compound CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 239000007848 Bronsted acid Substances 0.000 description 4
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 4
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- FDWREHZXQUYJFJ-UHFFFAOYSA-M gold monochloride Chemical compound [Cl-].[Au+] FDWREHZXQUYJFJ-UHFFFAOYSA-M 0.000 description 4
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- CZNGTXVOZOWWKM-UHFFFAOYSA-N methyl 4-bromobenzoate Chemical compound COC(=O)C1=CC=C(Br)C=C1 CZNGTXVOZOWWKM-UHFFFAOYSA-N 0.000 description 4
- IMNDHOCGZLYMRO-UHFFFAOYSA-N n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC=C1 IMNDHOCGZLYMRO-UHFFFAOYSA-N 0.000 description 4
- 150000002908 osmium compounds Chemical class 0.000 description 4
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical class Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 4
- VEDDBHYQWFOITD-UHFFFAOYSA-N para-bromobenzyl alcohol Chemical compound OCC1=CC=C(Br)C=C1 VEDDBHYQWFOITD-UHFFFAOYSA-N 0.000 description 4
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 150000003141 primary amines Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- LYDRKKWPKKEMNZ-UHFFFAOYSA-N tert-butyl benzoate Chemical compound CC(C)(C)OC(=O)C1=CC=CC=C1 LYDRKKWPKKEMNZ-UHFFFAOYSA-N 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 3
- 239000001149 (9Z,12Z)-octadeca-9,12-dienoate Substances 0.000 description 3
- JXNPEDYJTDQORS-HZJYTTRNSA-N (9Z,12Z)-octadecadien-1-ol Chemical compound CCCCC\C=C/C\C=C/CCCCCCCCO JXNPEDYJTDQORS-HZJYTTRNSA-N 0.000 description 3
- WTTJVINHCBCLGX-UHFFFAOYSA-N (9trans,12cis)-methyl linoleate Natural products CCCCCC=CCC=CCCCCCCCC(=O)OC WTTJVINHCBCLGX-UHFFFAOYSA-N 0.000 description 3
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 3
- RXEPBCWNHKZECN-UHFFFAOYSA-N 2-diphenylphosphanylethanamine Chemical compound C=1C=CC=CC=1P(CCN)C1=CC=CC=C1 RXEPBCWNHKZECN-UHFFFAOYSA-N 0.000 description 3
- LNJCGNRKWOHFFV-UHFFFAOYSA-N 3-(2-hydroxyethylsulfanyl)propanenitrile Chemical compound OCCSCCC#N LNJCGNRKWOHFFV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229910021583 Cobalt(III) fluoride Inorganic materials 0.000 description 3
- 239000005749 Copper compound Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 229910021577 Iron(II) chloride Inorganic materials 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- PKIXXJPMNDDDOS-UHFFFAOYSA-N Methyl linoleate Natural products CCCCC=CCCC=CCCCCCCCC(=O)OC PKIXXJPMNDDDOS-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000005595 acetylacetonate group Chemical group 0.000 description 3
- 150000001340 alkali metals Chemical group 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 150000001869 cobalt compounds Chemical class 0.000 description 3
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 3
- YCYBZKSMUPTWEE-UHFFFAOYSA-L cobalt(ii) fluoride Chemical compound F[Co]F YCYBZKSMUPTWEE-UHFFFAOYSA-L 0.000 description 3
- 150000001880 copper compounds Chemical class 0.000 description 3
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000003963 dichloro group Chemical group Cl* 0.000 description 3
- HDULBKVLSJEMGN-UHFFFAOYSA-N dicyclohexylphosphane Chemical compound C1CCCCC1PC1CCCCC1 HDULBKVLSJEMGN-UHFFFAOYSA-N 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 3
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 150000002344 gold compounds Chemical class 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 150000002504 iridium compounds Chemical class 0.000 description 3
- JXNPEDYJTDQORS-UHFFFAOYSA-N linoleyl alcohol Natural products CCCCCC=CCC=CCCCCCCCCO JXNPEDYJTDQORS-UHFFFAOYSA-N 0.000 description 3
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 3
- 229940073769 methyl oleate Drugs 0.000 description 3
- 150000002816 nickel compounds Chemical class 0.000 description 3
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 3
- YSIMAPNUZAVQER-UHFFFAOYSA-N octanenitrile Chemical compound CCCCCCCC#N YSIMAPNUZAVQER-UHFFFAOYSA-N 0.000 description 3
- 229940055577 oleyl alcohol Drugs 0.000 description 3
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- BSUSEPIPTZNHMN-UHFFFAOYSA-L cobalt(2+);diperchlorate Chemical compound [Co+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O BSUSEPIPTZNHMN-UHFFFAOYSA-L 0.000 description 1
- BGORGFZEVHFAQU-UHFFFAOYSA-L cobalt(2+);sulfate;hydrate Chemical compound O.[Co+2].[O-]S([O-])(=O)=O BGORGFZEVHFAQU-UHFFFAOYSA-L 0.000 description 1
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- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate trihydrate Substances [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
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- UMJDEUKQHKMAOI-UHFFFAOYSA-L dichlororuthenium;methylsulfinylmethane Chemical compound Cl[Ru]Cl.CS(C)=O.CS(C)=O.CS(C)=O.CS(C)=O UMJDEUKQHKMAOI-UHFFFAOYSA-L 0.000 description 1
- WIWBLJMBLGWSIN-UHFFFAOYSA-L dichlorotris(triphenylphosphine)ruthenium(ii) Chemical compound [Cl-].[Cl-].[Ru+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 WIWBLJMBLGWSIN-UHFFFAOYSA-L 0.000 description 1
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- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- PXCVPYJXMUOIMP-UHFFFAOYSA-N formaldehyde;ruthenium;triphenylphosphane Chemical compound [Ru].O=C.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 PXCVPYJXMUOIMP-UHFFFAOYSA-N 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- OVWPJGBVJCTEBJ-UHFFFAOYSA-K gold tribromide Chemical compound Br[Au](Br)Br OVWPJGBVJCTEBJ-UHFFFAOYSA-K 0.000 description 1
- IZLAVFWQHMDDGK-UHFFFAOYSA-N gold(1+);cyanide Chemical compound [Au+].N#[C-] IZLAVFWQHMDDGK-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000004129 indan-1-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])([H])C2([H])* 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910000398 iron phosphate Inorganic materials 0.000 description 1
- 229910000358 iron sulfate Inorganic materials 0.000 description 1
- NQXWGWZJXJUMQB-UHFFFAOYSA-K iron trichloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].Cl[Fe+]Cl NQXWGWZJXJUMQB-UHFFFAOYSA-K 0.000 description 1
- XBDUTCVQJHJTQZ-UHFFFAOYSA-L iron(2+) sulfate monohydrate Chemical compound O.[Fe+2].[O-]S([O-])(=O)=O XBDUTCVQJHJTQZ-UHFFFAOYSA-L 0.000 description 1
- MVFCKEFYUDZOCX-UHFFFAOYSA-N iron(2+);dinitrate Chemical compound [Fe+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MVFCKEFYUDZOCX-UHFFFAOYSA-N 0.000 description 1
- WBJZTOZJJYAKHQ-UHFFFAOYSA-K iron(3+) phosphate Chemical compound [Fe+3].[O-]P([O-])([O-])=O WBJZTOZJJYAKHQ-UHFFFAOYSA-K 0.000 description 1
- DYSQBHKDTAZKQW-DJFUMVPSSA-K iron(3+);(z)-1,1,1-trifluoro-4-oxopent-2-en-2-olate Chemical compound [Fe+3].CC(=O)\C=C(/[O-])C(F)(F)F.CC(=O)\C=C(/[O-])C(F)(F)F.CC(=O)\C=C(/[O-])C(F)(F)F DYSQBHKDTAZKQW-DJFUMVPSSA-K 0.000 description 1
- AQBLLJNPHDIAPN-LNTINUHCSA-K iron(3+);(z)-4-oxopent-2-en-2-olate Chemical compound [Fe+3].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O AQBLLJNPHDIAPN-LNTINUHCSA-K 0.000 description 1
- PVFSDGKDKFSOTB-UHFFFAOYSA-K iron(3+);triacetate Chemical compound [Fe+3].CC([O-])=O.CC([O-])=O.CC([O-])=O PVFSDGKDKFSOTB-UHFFFAOYSA-K 0.000 description 1
- XILAUHRDSUSGOG-UHFFFAOYSA-K iron(3+);trifluoride;trihydrate Chemical compound O.O.O.[F-].[F-].[F-].[Fe+3] XILAUHRDSUSGOG-UHFFFAOYSA-K 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- SHXXPRJOPFJRHA-UHFFFAOYSA-K iron(iii) fluoride Chemical compound F[Fe](F)F SHXXPRJOPFJRHA-UHFFFAOYSA-K 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- CQRPUKWAZPZXTO-UHFFFAOYSA-M magnesium;2-methylpropane;chloride Chemical compound [Mg+2].[Cl-].C[C-](C)C CQRPUKWAZPZXTO-UHFFFAOYSA-M 0.000 description 1
- IWCVDCOJSPWGRW-UHFFFAOYSA-M magnesium;benzene;chloride Chemical compound [Mg+2].[Cl-].C1=CC=[C-]C=C1 IWCVDCOJSPWGRW-UHFFFAOYSA-M 0.000 description 1
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 229910001463 metal phosphate Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- SEXOVMIIVBKGGM-UHFFFAOYSA-N naphthalene-1-thiol Chemical compound C1=CC=C2C(S)=CC=CC2=C1 SEXOVMIIVBKGGM-UHFFFAOYSA-N 0.000 description 1
- LAIZPRYFQUWUBN-UHFFFAOYSA-L nickel chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Ni+2] LAIZPRYFQUWUBN-UHFFFAOYSA-L 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 1
- RRIWRJBSCGCBID-UHFFFAOYSA-L nickel sulfate hexahydrate Chemical compound O.O.O.O.O.O.[Ni+2].[O-]S([O-])(=O)=O RRIWRJBSCGCBID-UHFFFAOYSA-L 0.000 description 1
- BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 description 1
- IPLJNQFXJUCRNH-UHFFFAOYSA-L nickel(2+);dibromide Chemical compound [Ni+2].[Br-].[Br-] IPLJNQFXJUCRNH-UHFFFAOYSA-L 0.000 description 1
- VCKGYYLUGUKTCX-UHFFFAOYSA-L nickel(2+);dichloride;trihydrate Chemical compound O.O.O.[Cl-].[Cl-].[Ni+2] VCKGYYLUGUKTCX-UHFFFAOYSA-L 0.000 description 1
- WHGYCGOFTBFDLW-UHFFFAOYSA-L nickel(2+);diperchlorate;hexahydrate Chemical compound O.O.O.O.O.O.[Ni+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O WHGYCGOFTBFDLW-UHFFFAOYSA-L 0.000 description 1
- KVRSDIJOUNNFMZ-UHFFFAOYSA-L nickel(2+);trifluoromethanesulfonate Chemical compound [Ni+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F KVRSDIJOUNNFMZ-UHFFFAOYSA-L 0.000 description 1
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 description 1
- DBJLJFTWODWSOF-UHFFFAOYSA-L nickel(ii) fluoride Chemical compound F[Ni]F DBJLJFTWODWSOF-UHFFFAOYSA-L 0.000 description 1
- BFSQJYRFLQUZKX-UHFFFAOYSA-L nickel(ii) iodide Chemical compound I[Ni]I BFSQJYRFLQUZKX-UHFFFAOYSA-L 0.000 description 1
- KFBKRCXOTTUAFS-UHFFFAOYSA-N nickel;triphenylphosphane Chemical compound [Ni].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 KFBKRCXOTTUAFS-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- IHUHXSNGMLUYES-UHFFFAOYSA-J osmium(iv) chloride Chemical compound Cl[Os](Cl)(Cl)Cl IHUHXSNGMLUYES-UHFFFAOYSA-J 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- ZVSLRJWQDNRUDU-UHFFFAOYSA-L palladium(2+);propanoate Chemical compound [Pd+2].CCC([O-])=O.CCC([O-])=O ZVSLRJWQDNRUDU-UHFFFAOYSA-L 0.000 description 1
- RFLFDJSIZCCYIP-UHFFFAOYSA-L palladium(2+);sulfate Chemical compound [Pd+2].[O-]S([O-])(=O)=O RFLFDJSIZCCYIP-UHFFFAOYSA-L 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- 229910000364 palladium(II) sulfate Inorganic materials 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 description 1
- XDASSWBZWFFNPX-UHFFFAOYSA-N palladium(ii) cyanide Chemical compound [Pd+2].N#[C-].N#[C-] XDASSWBZWFFNPX-UHFFFAOYSA-N 0.000 description 1
- HNNUTDROYPGBMR-UHFFFAOYSA-L palladium(ii) iodide Chemical compound [Pd+2].[I-].[I-] HNNUTDROYPGBMR-UHFFFAOYSA-L 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 1
- 238000007149 pericyclic reaction Methods 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- VXTFGYMINLXJPW-UHFFFAOYSA-N phosphinane Chemical group C1CCPCC1 VXTFGYMINLXJPW-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical group CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 1
- KGRJUMGAEQQVFK-UHFFFAOYSA-L platinum(2+);dibromide Chemical compound Br[Pt]Br KGRJUMGAEQQVFK-UHFFFAOYSA-L 0.000 description 1
- INXLGDBFWGBBOC-UHFFFAOYSA-N platinum(2+);dicyanide Chemical compound [Pt+2].N#[C-].N#[C-] INXLGDBFWGBBOC-UHFFFAOYSA-N 0.000 description 1
- ZXDJCKVQKCNWEI-UHFFFAOYSA-L platinum(2+);diiodide Chemical compound [I-].[I-].[Pt+2] ZXDJCKVQKCNWEI-UHFFFAOYSA-L 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- NEYLGXVZJUUZMY-UHFFFAOYSA-K potassium;trichlorogold Chemical compound [K].Cl[Au](Cl)Cl NEYLGXVZJUUZMY-UHFFFAOYSA-K 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- VXNYVYJABGOSBX-UHFFFAOYSA-N rhodium(3+);trinitrate Chemical compound [Rh+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VXNYVYJABGOSBX-UHFFFAOYSA-N 0.000 description 1
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- YEUGYZMSJJSMMP-UHFFFAOYSA-N ruthenium(2+);triphenylphosphane Chemical compound [Ru+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YEUGYZMSJJSMMP-UHFFFAOYSA-N 0.000 description 1
- MDODADMXKHLPIA-UHFFFAOYSA-N ruthenium(3+) hydrate Chemical compound O.[Ru+3] MDODADMXKHLPIA-UHFFFAOYSA-N 0.000 description 1
- BIXNGBXQRRXPLM-UHFFFAOYSA-K ruthenium(3+);trichloride;hydrate Chemical compound O.Cl[Ru](Cl)Cl BIXNGBXQRRXPLM-UHFFFAOYSA-K 0.000 description 1
- LJZVDOUZSMHXJH-UHFFFAOYSA-K ruthenium(3+);triiodide Chemical compound [Ru+3].[I-].[I-].[I-] LJZVDOUZSMHXJH-UHFFFAOYSA-K 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- VIHDTGHDWPVSMM-UHFFFAOYSA-N ruthenium;triphenylphosphane Chemical compound [Ru].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 VIHDTGHDWPVSMM-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
- 229940071536 silver acetate Drugs 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 1
- 229910001958 silver carbonate Inorganic materials 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- KKKDGYXNGYJJRX-UHFFFAOYSA-M silver nitrite Chemical compound [Ag+].[O-]N=O KKKDGYXNGYJJRX-UHFFFAOYSA-M 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- YPNVIBVEFVRZPJ-UHFFFAOYSA-L silver sulfate Chemical compound [Ag+].[Ag+].[O-]S([O-])(=O)=O YPNVIBVEFVRZPJ-UHFFFAOYSA-L 0.000 description 1
- 229910000367 silver sulfate Inorganic materials 0.000 description 1
- 229910001494 silver tetrafluoroborate Inorganic materials 0.000 description 1
- KZJPVUDYAMEDRM-UHFFFAOYSA-M silver;2,2,2-trifluoroacetate Chemical compound [Ag+].[O-]C(=O)C(F)(F)F KZJPVUDYAMEDRM-UHFFFAOYSA-M 0.000 description 1
- JUDUFOKGIZUSFP-UHFFFAOYSA-M silver;4-methylbenzenesulfonate Chemical compound [Ag+].CC1=CC=C(S([O-])(=O)=O)C=C1 JUDUFOKGIZUSFP-UHFFFAOYSA-M 0.000 description 1
- CLDWGXZGFUNWKB-UHFFFAOYSA-M silver;benzoate Chemical compound [Ag+].[O-]C(=O)C1=CC=CC=C1 CLDWGXZGFUNWKB-UHFFFAOYSA-M 0.000 description 1
- GJGOWHNOGHVUJK-UHFFFAOYSA-M silver;pyridine-2-carboxylate Chemical compound [Ag+].[O-]C(=O)C1=CC=CC=N1 GJGOWHNOGHVUJK-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 1
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ZSSMIQURWRIOCN-UHFFFAOYSA-N tert-butyl(phenyl)phosphane Chemical compound CC(C)(C)PC1=CC=CC=C1 ZSSMIQURWRIOCN-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 1
- MJRFDVWKTFJAPF-UHFFFAOYSA-K trichloroiridium;hydrate Chemical compound O.Cl[Ir](Cl)Cl MJRFDVWKTFJAPF-UHFFFAOYSA-K 0.000 description 1
- UACQLNPCDXDCID-UHFFFAOYSA-K trichloroosmium;trihydrate Chemical compound O.O.O.Cl[Os](Cl)Cl UACQLNPCDXDCID-UHFFFAOYSA-K 0.000 description 1
- TYLYVJBCMQFRCB-UHFFFAOYSA-K trichlororhodium;trihydrate Chemical compound O.O.O.[Cl-].[Cl-].[Cl-].[Rh+3] TYLYVJBCMQFRCB-UHFFFAOYSA-K 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- GCZKMPJFYKFENV-UHFFFAOYSA-K triiodogold Chemical compound I[Au](I)I GCZKMPJFYKFENV-UHFFFAOYSA-K 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JQZIKLPHXXBMCA-UHFFFAOYSA-N triphenylmethanethiol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(S)C1=CC=CC=C1 JQZIKLPHXXBMCA-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
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- C07C323/25—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
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- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/29—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
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- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
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- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
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Description
[1]下記一般式(1A)で表される化合物。
で表される1価基及び下記一般式(GS)
で表される1価基から構成される群より選択される基を表す。]
[2]前記R5〜R15がいずれも水素原子である、前記[1]に記載の化合物。
[3]光学活性体である、前記[1]又は前記[2]に記載の化合物。
[4]下記一般式(2A)
で表される化合物と、下記一般式(3)
で表される化合物を反応させる、前記[1]〜[3]のいずれか1つに記載の化合物の製造方法。
[5]下記一般式(2A)で表される化合物。
[6]前記R5〜R15がいずれも水素原子である、前記[5]に記載の化合物。
[7]光学活性体である、前記[5]又は前記[6]に記載の化合物。
[8]前記[1]〜[3]のいずれか1つに記載の化合物を配位子として有する遷移金属錯体。
[9]金属種が、第8〜11族遷移金属から構成される群より選択される金属種である、前記[8]に記載の遷移金属錯体。
[10]前記金属種が、第8族遷移金属から選択される金属種である、前記[9]に記載の遷移金属錯体。
例えば、一般式(1A)で表される化合物を配位子として有するルテニウム錯体は、従来の簡便に製造可能な四座配位子を有するルテニウム錯体に比べて、エステル類の水素添加反応において優れた触媒活性を示すことから、この反応によって工業的に価値の高い1級アルコール類を効率良く製造することが出来る。
以下、一般式(1A)で表される化合物(以下、本発明の化合物(1A)と称す)について詳細に説明する。
前記一般式(1A)中、実線は単結合、二重線は二重結合を表す。Cは炭素原子、Hは水素原子、Nは窒素原子を表す。R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14及びR15は各々独立して、水素原子、アルキル基、シクロアルキル基、アリール基及びアラルキル基から構成される群より選択される基を表す。Gは、前記一般式(GP)で表される1価基及び前記一般式(GS)で表される1価基から構成される群より選択される基を表す。前記一般式(GP)及び一般式(GS)中、実線は単結合、点線は配位結合、波線が交差した実線は隣接する原子への結合手を表す。Pはリン原子、Sは硫黄原子を表す。Lは孤立電子対又は三水素化ホウ素を表す。R1、R2及びR3は各々独立して、アルキル基、シクロアルキル基、置換基を有してもよいアルケニル基、置換基を有してもよいアリール基、置換基を有してもよいヘテロアリール基及び置換基を有してもよいアラルキル基から構成される群より選択される基を表し、好ましくはアルキル基、シクロアルキル基及び置換基を有してもよいアリール基から構成される群より選択される基を表す。
これらの置換基におけるアルコキシ基としては、例えば炭素数1〜10のアルコキシ基、好ましくは炭素数1〜4のアルコキシ基が挙げられ、具体的にはメトキシ基、エトキシ基、1−プロポキシ基、2−プロポキシ基、1−ブトキシ基、2−ブトキシ基及びtert−ブトキシ基等が挙げられる。
これらの置換基におけるシリル基としては、例えば炭素数3〜36のシリル基、好ましくは炭素数3〜18のシリル基が挙げられ、具体的にはトリメチルシリル基、トリエチルシリル基、tert−ブチルジメチルシリル基、トリ(2−プロピル)シリル基、tert−ブチルジフェニルシリル基及びトリフェニルシリル基等が挙げられる。
これらの置換基におけるハロゲノ基としては、具体的にはフルオロ基、クロロ基、ブロモ基及びヨード基等が挙げられ、好ましくはフルオロ基及びクロロ基等が挙げられる。
で表される化合物(以下、化合物(1B)と称す)が挙げられる。
次に、本発明の化合物(1A)の原料化合物となる、一般式(2A)で表される化合物(以下、本発明の中間体(2A)と称す)について説明する。
前記一般式(2A)中、実線は単結合、二重線は二重結合を表す。Cは炭素原子、Nは窒素原子、Oは酸素原子を表す。R4〜R15は、前記一般式(1A)において定義したR4〜R15と同様の基である。
で表される化合物(以下、化合物(2B)と称す)が挙げられる。
で表される化合物(以下、化合物(4A)と称す)と、下記一般式(5A)
で表される化合物(以下、化合物(5A)と称す)を、塩基性条件下で反応させることによって容易に得ることが出来る。
で表される化合物(以下、化合物(4B)と称す)と、下記一般式(5B)
で表される化合物(以下、化合物(5B)と称す)を、塩基性条件下で反応させることによって容易に得ることが出来る。
次に、本発明の化合物(1A)の製造方法について詳細に説明する。本発明の化合物(1A)は、本発明の中間体(2A)と、一般式(3)で表される化合物(以下、化合物(3)と称す)との反応によって容易に得ることが出来る(Eq.2)。
前記一般式(3)中、実線は単結合を表す。Hは水素原子を表す。Gは、前記一般式(1A)において定義したGと同様の基を表す。
化合物(3)としては、具体的には下記一般式(3P)
で表される化合物(以下、化合物(3P)と称す)、即ち2級ホスフィン及び2級ホスフィン−三水素化ホウ素錯体並びに、下記一般式(3S)
で表される化合物(以下、化合物(3S)と称す)、即ちチオールが挙げられる。
本反応を塩基性条件にて実施する場合、好ましい塩基としては、具体的には水酸化リチウム、水酸化ナトリウム及び水酸化カリウム等のアルカリ金属水酸化物、リン酸ナトリウム及びリン酸カリウム等のアルカリ金属リン酸塩、炭酸リチウム、炭酸ナトリウム及び炭酸カリウム等のアルカリ金属炭酸塩、酢酸ナトリウム及び酢酸カリウム等のアルカリ金属カルボン酸塩、水酸化カルシウム、水酸化ストロンチウム及び水酸化バリウム等のアルカリ土類金属水酸化物、水素化リチウム、水素化ナトリウム、水素化カリウム、水素化カルシウム、水素化ホウ素ナトリウム及び水素化アルミニウムリチウム等の金属水素化物、リチウムメトキシド、ナトリウムメトキシド、カリウムメトキシド、ナトリウムエトキシド、カリウムエトキシド、ナトリウム−tert−ブトキシド及びカリウム−tert−ブトキシド等のアルカリ金属アルコキシド、メチルリチウム、n−ブチルリチウム、sec−ブチルリチウム、tert−ブチルリチウム及びフェニルリチウム等の有機リチウム化合物、リチウムアミド、ナトリウムアミド、リチウムジイソプロピルアミド及びリチウムヘキサメチルジシラジド等のアルカリ金属アミド類、塩化メチルマグネシウム、塩化tert−ブチルマグネシウム、塩化フェニルマグネシウム、臭化フェニルマグネシウム及びヨウ化メチルマグネシウム等のグリニャール試薬、トリエチルアミン、トリ−n−ブチルアミン、ジイソプロピルエチルアミン、N,N−ジメチルアニリン、4−ジメチルアミノピリジン、ピロリジン、ピペリジン、N−メチルモルホリン、1,5−ジアザビシクロ[4.3.0]ノナ−5−エン及び1,8−ジアザビシクロ[5.4.0]ウンデカ−7−エン等のアミン類等が挙げられ、好ましい具体例としてはn−ブチルリチウムが挙げられる。これらの塩基は、各々単独で用いても2種以上適宜組み合わせて用いてもよい。
なお、本反応において塩基の添加方法は特に限定されるものではないが、化合物(3)と塩基を各々単独に添加してもよく、化合物(3)と塩基(及び溶媒)の混合物として添加してもよく、化合物(3)と塩基を(溶媒中にて)反応させることによって得られる、前記2級ホスフィド、2級ホスフィド−3水素化ホウ素錯体又はチオラートとして添加してもよい。従って、化合物(3)の代替として前記2級ホスフィド、2級ホスフィド−3水素化ホウ素錯体又はチオラートを本発明の中間体(2A)と反応させる際には、塩基を添加せずに反応を実施してもよい。
反応温度は、通常−78℃〜200℃、好ましくは−20℃〜175℃、より好ましくは0℃〜150℃の範囲から適宜選択される。
反応時間は、塩基、溶媒及び反応温度その他の条件によって異なるが、通常1分〜24時間、好ましくは2分〜12時間、より好ましくは5分〜8時間の範囲から適宜選択される。
次に、本発明の遷移金属錯体について詳細に説明する。本発明の遷移金属錯体における金属種としては、本発明の化合物(1A)が配位可能であれば特に制限は無いが、有機合成反応における触媒活性の観点からは、好ましくは第8〜11族遷移金属から構成される群より選択される金属種が挙げられ、より好ましくは第8族遷移金属から選択される金属種が挙げられ、特に好ましい金属種としては鉄及びルテニウム等が挙げられる。
精製及び単離の方法としては例えば、吸着剤による脱色、カラムクロマトグラフィー、晶析及び昇華等が挙げられ、これらを単独で或いは併用して行ってもよい。
2)炭素13核磁気共鳴分光法(13C NMR):400MR DD2型装置(共鳴周波数:100MHz、アジレント社製)
3)リン31核磁気共鳴分光法(31P NMR):400MR DD2型装置(共鳴周波数:161MHz、アジレント社製)
4)精密質量分析(HRMS):JMS−T100GCV型装置(日本電子株式会社製)
5)ガスクロマトグラフィー(GC):GC−4000型装置(ジーエルサイエンス社製)及びGC−4000Plus型装置(ジーエルサイエンス社製)
[測定条件1]装置:GC−4000型装置、カラム:InertCap1(ジーエルサイエンス社製)、試料導入部:250℃、試料検出部:250℃、初期温度:50℃、昇温速度:10℃/分、到達温度:250℃、到達温度保持時間:0分。
[測定条件2]GC測定条件1において、装置としてGC−4000Plus型装置を用い、到達温度保持時間を0分から10分に延長した。
3,3’−[1,2−フェニレンビス(メチレン)]ビス(2−オキサゾリジノン)(構造式(2B−1))の合成(Eq.4)
13C NMR(100MHz,CDCl3):δ=158.35,134.15,129.26,128.49,61.83,45.47,44.20.
3,3’−[1,2−フェニレンビス(メチレン)]ビス[(S)−4−イソプロピル−2−オキサゾリジノン](構造式((S,S)−2B−2))の合成(Eq.5)
13C NMR(100MHz,CDCl3):δ=158.64,134.08,128.72,128.14,62.85,59.27,43.24,27.47,17.74,14.08.
3,3’−[1,2−フェニレンビス(メチレン)]ビス[(S)−4−フェニル−2−オキサゾリジノン](構造式((S,S)−2B−3))の合成(Eq.6)
13C NMR(100MHz,CDCl3):δ=158.20,137.17,133.88,129.56,129.28,129.07,128.27,126.94,69.90,59.24,42.37.
3,3’−[1,2−フェニレンビス(メチレン)]ビス[(S)−4−ベンジル−2−オキサゾリジノン](構造式((S,S)−2B−4))の合成(Eq.7)
13C NMR(100MHz,CDCl3):δ=158.22,135.22,134.34,128.92,128.90,128.30,127.18,66.99,56.45,43.97,38.61.
N,N’−[1,2−フェニレンビス(メチレン)]ビス[2−(ジフェニルホスフィノ)エチルアミン](構造式(1B−1))の合成(Eq.8)
(仕込み・反応)500mL四つ口丸底フラスコに、マグネティックスターラーバー、50mL滴下漏斗、温度計及び三方コックを取り付けて内部を窒素置換し、ジフェニルホスフィン(3P−9)(純度:98.5%、10.0g、純量:9.85g、52.9mmol、2.2当量)及び脱水THF(53mL)を順次仕込み、得られた溶液をマグネティックスターラーで攪拌しながら、氷水浴にて5℃に冷却した。次いで、n−ブチルリチウム(n−BuLi)のn−ヘキサン溶液(濃度:1.61mol/L、32.9mL、52.9mmol、2.2当量)を滴下漏斗に仕込み、内温が10℃以下を保つ速度で20分かけて滴下した。その後、氷水浴を取り去って室温で20分攪拌することで、リチウムジフェニルホスフィドのTHF/n−ヘキサン溶液(52.9mmol、2.2当量)が赤橙色液体として得られた。
(仕込み・反応)500mL四つ口丸底フラスコに、マグネティックスターラーバー、200mL滴下漏斗、温度計及び三方コックを取り付けて内部を窒素置換し、実施例1で得られた3,3’−[1,2−フェニレンビス(メチレン)]ビス(2−オキサゾリジノン)(2B−1)(6.64g、24.0mmol、1.0当量)及び脱水THF(72mL)を順次仕込み、得られた白色の懸濁液をマグネティックスターラーで攪拌した。次いで、第1工程で得られたリチウムジフェニルホスフィドのTHF/n−ヘキサン溶液(52.9mmol、2.2当量)を滴下漏斗に仕込み、内温が30℃以下を保つ速度で30分かけて滴下した。その後、得られた赤橙色の反応液を室温で1時間攪拌した。
31P NMR(161MHz,CDCl3):δ=−20.83(s,2P).
(1S,1’S)−N,N’−[1,2−フェニレンビス(メチレン)]ビス[2−(ジフェニルホスフィノ)−1−イソプロピル−エチルアミン](構造式((S,S)−1B−2))
の合成(Eq.9)
31P NMR(161MHz,CDCl3):δ=−21.95(s,2P).
(1S,1’S)−N,N’−[1,2−フェニレンビス(メチレン)]ビス[2−(ジフェニルホスフィノ)−1−フェニル−エチルアミン](構造式((S,S)−1B−3))の合成(Eq.10)
31P NMR(161MHz,CDCl3):δ=−23.18(s,2P).
(1S,1’S)−N,N’−[1,2−フェニレンビス(メチレン)]ビス[2−(ジフェニルホスフィノ)−1−ベンジル−エチルアミン](構造式((S,S)−1B−4))の合成(Eq.11)
31P NMR(161MHz,CDCl3):δ=−23.32(s,2P).
N,N’−[1,2−フェニレンビス(メチレン)]ビス[2−(ジシクロヘキシルホスフィノ)エチルアミン]ビスボラート(構造式(1B−5))の合成(Eq.12)
(仕込み・反応)200mL四つ口丸底フラスコに、マグネティックスターラーバー、20mL滴下漏斗、温度計及び三方コックを取り付けて内部を窒素置換し、ジシクロヘキシルホスフィン(3P−6)(20.0mL、91.2mmol、1.0当量)及び脱水ジエチルエーテル(Et2O)(100mL)を順次仕込み、得られた溶液をマグネティックスターラーで攪拌しながら、氷水浴にて5℃に冷却した。次いで、3水素化ホウ素−ジメチルスルフィド錯体(BH3−SMe2)(濃度:10.0mol/L、13.7mL、137.0mmol、1.5当量)を滴下漏斗に仕込み、内温が10℃以下を保つ速度で10分かけて溶液に滴下した後、反応液を常温まで昇温させた。
(仕込み・反応)100mL四つ口丸底フラスコに、マグネティックスターラーバー、20mL滴下漏斗、温度計及び三方コックを取り付けて内部を窒素置換し、第1工程で得られたジシクロヘキシルホスフィン−3水素化ホウ素錯体(3P−21)(6.0g、28.3mmol、2.2当量)及び脱水THF(28mL)を順次仕込み、得られた溶液をマグネティックスターラーで攪拌しながら、氷水浴にて5℃に冷却した。次いで、n−BuLiのn−ヘキサン溶液(濃度:1.61mol/L、17.6mL、28.3mmol、2.2当量)を滴下漏斗に仕込み、内温が10℃以下を保つ速度で20分かけて滴下した。その後、氷水浴を取り去って室温で20分攪拌することで、リチウムジシクロヘキシルホスフィド−3水素化ホウ素錯体/n−ヘキサン/THF混合物(28.3mmol、2.2当量)が白色懸濁液として得られた。
(仕込み・反応)200mL四つ口丸底フラスコに、マグネティックスターラーバー、100mL滴下漏斗、温度計及び三方コックを取り付けて内部を窒素置換し、実施例1で得られた3,3’−[1,2−フェニレンビス(メチレン)]ビス(2−オキサゾリジノン)(2B−1)(3.6g、12.9mmol、1.0当量)及び脱水THF(39mL)を順次仕込み、得られた白色懸濁液をマグネティックスターラーで攪拌した。次いで、第2工程で得られたリチウムジシクロヘキシルホスフィド−3水素化ホウ素錯体/n−ヘキサン/THF混合物(28.3mmol、2.2当量)を、脱水THF(15mL)を用いて滴下漏斗に移送し、内温が30℃以下を保つ速度で30分かけて滴下した。その後、得られた薄黄色の反応液を室温で1時間攪拌した。
31P NMR(161MHz,CDCl3):δ=22.56(d,J=58.0Hz,2P).
N,N’−[1,2−フェニレンビス(メチレン)]ビス[2−(メチルチオ)エチルアミン](構造式(1B−6))の合成(Eq.13)
13C NMR(100MHz,CDCl3):δ=138.74,130.07,127.32,51.80,47.58,34.45,15.31.
N,N’−[1,2−フェニレンビス(メチレン)]ビス[2−(p−トリルチオ)エチルアミン](構造式(1B−7))の合成(Eq.14)
13C NMR(100MHz,CDCl3):δ=138.69,136.28,132.06,130.34,130.07,129.68,51.70,47.92,34.86,20.98.
(1S,1’S)−N,N’−[1,2−フェニレンビス(メチレン)]ビス[2−(p−トリルチオ)−1−ベンジル−エチルアミン](構造式((S,S)−1B−8))の合成(Eq.15)
13C NMR(100MHz,CDCl3):δ=138.78,138.47,136.00,132.71,129.93,129.71,129.65,129.32,128.38,127.17,126.26,57.98,48.97,40.06,38.40,20.97.
cis−α−ジクロロ{N,N’−[1,2−フェニレンビス(メチレン)]ビス[2−(ジフェニルホスフィノ)エチルアミン]}ルテニウム(II)(構造式(cis−α−RuCl2(1B−1)))の合成(Eq.16)
31P NMR(161MHz,CDCl3):δ=60.10(s,2P).
HRMS:質量電荷比(以下、m/zと略す)=732.0936,表題化合物の分子量イオン組成式(以下、Mと略す)=C36H38Cl2N2P2Ru.
cis−β−ジクロロ{N,N’−[1,2−フェニレンビス(メチレン)]ビス[2−(ジフェニルホスフィノ)エチルアミン]}ルテニウム(II)(構造式(cis−β−RuCl2(1B−1)))の合成(Eq.17)
31P NMR(161MHz,CD2Cl2):δ=60.72(d,J=34.0Hz,1P),53.34(d,J=34.0Hz,1P).
クロロヒドリド{N,N’−[1,2−フェニレンビス(メチレン)]ビス[2−(ジフェニルホスフィノ)エチルアミン]}ルテニウム(II)(構造式(RuHCl(1B−1)))の合成(Eq.18)
31P NMR(161MHz,C6D6):δ=77.50(major,s,1.6P),77.35(minor,s,0.4P).
NMR測定により、表題化合物はRu−H結合を有することと、2種類の配位異性体混合物であることが明らかとなった。
ヒドリドボロヒドリド{N,N’−[1,2−フェニレンビス(メチレン)]ビス[2−(ジフェニルホスフィノ)エチルアミン]}ルテニウム(II)(構造式(RuH(BH4)(1B−1)))の合成(Eq.19)
31P NMR(161MHz,C6D6):δ=80.80(major,br s,1.4P),80.12(minor,br s,0.6P).
NMR測定により、表題化合物はRu−H結合及びRu−η1−BH4結合を有することと、2種類の配位異性体混合物であることがわかった。
ジベンゾアト{N,N’−[1,2−フェニレンビス(メチレン)]ビス[2−(ジフェニルホスフィノ)エチルアミン]}ルテニウム(II)(構造式(Ru(OBz)2(1B−1)))の合成(Eq.20)
31P NMR測定により、表題化合物は2種類の配位異性体混合物であることが明らかとなった。
ジピバラト{N,N’−[1,2−フェニレンビス(メチレン)]ビス[2−(ジフェニルホスフィノ)エチルアミン]}ルテニウム(II)(構造式(Ru(OPiv)2(1B−1)))の合成(Eq.21)
(仕込み・反応)200mL四つ口丸底フラスコに、マグネティックスターラーバー、滴下漏斗、温度計及び三方コックを取り付けた後に窒素置換し、ピバリン酸(3.67g、35.9mmol、4.4当量)及び脱水メタノール(60mL)を順次仕込み、得られた溶液をマグネティックスターラーを用いて室温にて攪拌した。次いで、滴下漏斗にナトリウムメトキシドのメタノール溶液(濃度:28.4%、6.52g、純量:1.85g、34.3mmol、4.2当量)を仕込み、内温が30℃以下を保つ速度で15分かけて滴下した後、滴下漏斗を脱水メタノール(5mL)にて共洗した。得られた反応液を室温で30分攪拌した後、[RuCl2(p−cymene)]2(5.0g、8.16mmol、1.0当量)を投入し、室温で3時間攪拌した。
(仕込み・反応)50mL四つ口反応フラスコに、マグネティックスターラーバー、冷却管、温度計及び三方コックを取り付けて内部を窒素置換し、実施例5で得られたN,N’−[1,2−フェニレンビス(メチレン)]ビス[2−(ジフェニルホスフィノ)エチルアミン](1B−1)のトルエン溶液(純度:20.0%、2.50g、純量:500mg、0.892mmol、1.1当量)、脱水トルエン(16mL)及び第1工程で得られたRu(OPiv)2(p−cymene)(355mg、0.811mmol、1.0当量)を順次仕込み、得られた溶液をマグネティックスターラーで攪拌しながら、油浴を用いて加熱し、還流条件で8時間攪拌した。
31P NMR測定により、表題化合物は2種類の配位異性体混合物であることが明らかとなった。
ジクロロ{(1S,1’S)−N,N’−[1,2−フェニレンビス(メチレン)]ビス[2−(ジフェニルホスフィノ)−1−イソプロピル−エチルアミン]}ルテニウム(II)(構造式(RuCl2[(S,S)−1B−2]))の合成(Eq.22)
HRMS:m/z=816.1876,M=C42H50Cl2N2P2Ru.
なお、表題化合物の1H NMR測定を行ったところ、0〜8ppmの範囲に亘ってブロードなピークが観測された。2つのイソプロピル基の立体障害によって分子運動が阻害されているためと推測される。
ジクロロ{N,N’−[1,2−フェニレンビス(メチレン)]ビス[2−(メチルチオ)エチルアミン]}ルテニウム(II)(構造式(RuCl2(1B−6)))の合成(Eq.23)
なお、1H NMR分析によって、表題化合物は配位異性体混合物であることが判明した。この配位異性現象は、硫黄原子上の2つの孤立電子対に由来するものと考えられる。
ジクロロ{N,N’−[1,2−フェニレンビス(メチレン)]ビス[2−(p−トリルチオ)エチルアミン]}ルテニウム(II)(構造式(RuCl2(1B−7)))の合成(Eq.24)
なお、1H NMR分析によって、表題化合物は実施例20同様に配位異性体混合物であることが判明した。
ジクロロ{(1S,1’S)−N,N’−[1,2−フェニレンビス(メチレン)]ビス[2−(p−トリルチオ)−1−ベンジル−エチルアミン]}ルテニウム(II)(構造式(RuCl2[(S,S)−1B−8])の合成)(Eq.25)
なお、1H NMR分析によって、表題化合物は実施例20及び実施例21同様、配位異性体混合物であることが判明した。
ジクロロ{N,N’−[1,2−フェニレンビス(メチレン)]ビス[2−(ジフェニルホスフィノ)エチルアミン]}鉄(II)(構造式(FeCl2(1B−1)))の合成(Eq.26)
1H NMR測定の結果、−5〜150ppmという幅広い範囲に亘ってブロードなピークが観測されたことから、表題化合物は常磁性であると判明した。また、−150〜250ppmの範囲においては、31P NMRではピークが観測されなかった。
ジクロロ{(1S,1’S)−N,N’−[1,2−フェニレンビス(メチレン)]ビス[2−(ジフェニルホスフィノ)−1−フェニル−エチルアミン]}鉄(II)(構造式(FeCl2[(S,S)−1B−3]))の合成(Eq.27)
1H NMR測定の結果、−10〜140ppmという幅広い範囲に亘ってブロードなピークが観測されたことから、表題化合物は常磁性であると判明した。また、−150〜250ppmの範囲においては、31P NMRではピークが観測されなかった。
安息香酸メチルの触媒的水素添加反応によるベンジルアルコールの製造(1)(Eq.28)
GC保持時間(測定条件1);安息香酸メチル:6.81分、ベンジルアルコール:5.84分。
安息香酸メチルの触媒的水素添加反応によるベンジルアルコールの製造(2)
溶媒として脱水トルエンを用いた以外は、実施例25と同様にしてベンジルアルコールを製造した。転化率:94.0%、選択率:98.7%。
安息香酸メチルの触媒的水素添加反応によるベンジルアルコールの製造(3)
触媒として実施例14で得られたcis−β−RuCl2(1B−1)を用いた以外は、実施例25と同様にしてベンジルアルコールを製造した。転化率:93.7%、選択率:99.1%。
安息香酸メチルの触媒的水素添加反応によるベンジルアルコールの製造(4)
触媒として実施例16で得られたRuH(BH4)(1B−1)を用い、塩基であるKOt−BuのTHF溶液を添加することなく、水素圧を5MPaとした以外は、実施例25と同様にしてベンジルアルコールを製造した。転化率:>99.9%、選択率:>99.9%。
安息香酸メチルの触媒的水素添加反応によるベンジルアルコールの製造(5)
触媒として、実施例20で得られたRuCl2(1B−6)を用い、水素圧を5MPaとした以外は、実施例25と同様にしてベンジルアルコールを製造した。転化率:94.8%、選択率:98.7%。
更に、配位形式の異なるcis−β−RuCl2(1B−1)もまた、cis−α体同様の優れた触媒活性を有していた(実施例27)。
従ってこれらの錯体は、従来のPNNP四座配位子を有するルテニウム錯体(前記の特許文献1及び非特許文献1)と比較して、大幅に触媒活性が向上していることがわかる。
また、本発明の遷移金属錯体の中でも、SNNS四座配位子を有するルテニウム錯体であるRuCl2(1B−6)は、5MPaという高圧の水素ガスを必要とするものの、従来のSNNS四座配位子を有する従来のルテニウム錯体(前記の非特許文献2)ではそもそも困難だった、ケトン類よりも反応性に乏しいエステル類の水素添加反応を効率よく進行させることが明らかとなった(実施例29)。
安息香酸tert−ブチルの触媒的水素添加反応によるベンジルアルコールの製造(Eq.29)
GC保持時間(測定条件1);安息香酸tert−ブチル:9.02分、ベンジルアルコール:5.73分。
N,N−ジメチルベンズアミドの触媒的水素添加反応によるベンジルアルコールの製造(Eq.30)
GC保持時間(測定条件2);N,N−ジメチルベンズアミド:10.56分、ベンジルアルコール:6.15分。
4−ブロモ安息香酸メチルの触媒的水素添加反応による4−ブロモベンジルアルコールの製造(Eq.31)
GC保持時間(測定条件2);4−ブロモ安息香酸メチル:10.44分、4−ブロモベンジルアルコール:10.15分。
(4E)−デセン酸エチルの触媒的水素添加反応による(4E)−デセン−1−オールの製造(Eq.32)
GC保持時間(測定条件2);(4E)−デセン酸エチル:11.03分、(4E)−デセン−1−オール:9.41分。
オレイン酸メチルの触媒的水素添加反応によるオレイルアルコールの製造(Eq.33)
GC保持時間(測定条件2);オレイン酸メチル:18.69分、オレイルアルコール:18.35分。
リノール酸メチルの触媒的水素添加反応によるリノレイルアルコールの製造(Eq.34)
GC保持時間(測定条件2);リノール酸メチル:18.61分、リノレイルアルコール:18.24分。
中性条件下での3−[(tert−ブトキシカルボニル)アミノ]酪酸メチルの触媒的水素添加反応によるtert−ブチル(4−ヒドロキシブタン−2−イル)カーバメートの製造(Eq.35)
GC保持時間(測定条件2);3−[(tert−ブトキシカルボニル)アミノ]酪酸メチル:10.60分、tert−ブチル(4−ヒドロキシブタン−2−イル)カーバメート:10.12分。
中性条件下でのγ−ブチロラクトンの触媒的水素添加反応による1,4−ブタンジオールの製造(Eq.36)
GC保持時間(測定条件2);γ−ブチロラクトン:4.24分、1,4−ブタンジオール:4.89分。
ベンゾニトリルの触媒的水素添加反応によるベンジルアミンの合成(Eq.37)
GC保持時間(測定条件2);ベンゾニトリル:5.49分、ベンジルアミン:5.87分。
1−オクタンニトリルの触媒的水素添加反応による1−オクチルアミンの合成(Eq.38)
GC保持時間(測定条件2);1−オクタンニトリル:6.67分、1−オクチルアミン:6.46分。
Claims (8)
- 下記一般式(1A)で表される化合物。
で表される1価基及び下記一般式(GS)
で表される1価基から構成される群より選択される基を表す。] - 光学活性体である、請求項1に記載の化合物。
- 光学活性体である、請求項4に記載の化合物。
- 請求項1又は2に記載の化合物を配位子として有する遷移金属錯体。
- 金属種が、第8〜11族遷移金属から構成される群より選択される金属種である、請求項6に記載の遷移金属錯体。
- 前記金属種が、第8族遷移金属から選択される金属種である、請求項7に記載の金属錯体。
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