JP6499646B2 - アルキンのルテニウム触媒トランス選択的ヒドロスズ化方法 - Google Patents
アルキンのルテニウム触媒トランス選択的ヒドロスズ化方法 Download PDFInfo
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- JP6499646B2 JP6499646B2 JP2016525574A JP2016525574A JP6499646B2 JP 6499646 B2 JP6499646 B2 JP 6499646B2 JP 2016525574 A JP2016525574 A JP 2016525574A JP 2016525574 A JP2016525574 A JP 2016525574A JP 6499646 B2 JP6499646 B2 JP 6499646B2
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- 150000001345 alkine derivatives Chemical class 0.000 title claims description 63
- -1 cyclic aliphatic hydrocarbons Chemical class 0.000 claims description 117
- 125000000217 alkyl group Chemical group 0.000 claims description 84
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 75
- 239000003054 catalyst Substances 0.000 claims description 73
- 229930195733 hydrocarbon Natural products 0.000 claims description 58
- 238000000034 method Methods 0.000 claims description 58
- 125000004432 carbon atom Chemical group C* 0.000 claims description 53
- 125000005842 heteroatom Chemical group 0.000 claims description 53
- 239000004215 Carbon black (E152) Substances 0.000 claims description 47
- 125000001424 substituent group Chemical group 0.000 claims description 47
- 125000003118 aryl group Chemical group 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 28
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- 125000001931 aliphatic group Chemical group 0.000 claims description 23
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 23
- 230000008569 process Effects 0.000 claims description 21
- 229910052707 ruthenium Inorganic materials 0.000 claims description 21
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 20
- 150000002430 hydrocarbons Chemical class 0.000 claims description 20
- 230000000707 stereoselective effect Effects 0.000 claims description 20
- KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical compound [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 239000003446 ligand Substances 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000000129 anionic group Chemical group 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 229910000083 tin tetrahydride Inorganic materials 0.000 claims description 9
- 239000012327 Ruthenium complex Substances 0.000 claims description 8
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 8
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 150000001336 alkenes Chemical class 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 7
- 150000001408 amides Chemical class 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical group 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 229910020366 ClO 4 Inorganic materials 0.000 claims description 3
- 229910018286 SbF 6 Inorganic materials 0.000 claims description 3
- 239000000539 dimer Substances 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 3
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 3
- 150000001993 dienes Chemical class 0.000 claims description 2
- 241000162682 Heterogen Species 0.000 claims 1
- 238000003763 carbonization Methods 0.000 claims 1
- 238000005481 NMR spectroscopy Methods 0.000 description 151
- 239000012230 colorless oil Substances 0.000 description 33
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 31
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 19
- 239000000758 substrate Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- 229910052718 tin Inorganic materials 0.000 description 13
- 238000007792 addition Methods 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- 125000000524 functional group Chemical group 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 0 CC(C(N)=C(*)C(*)=O)=O Chemical compound CC(C(N)=C(*)C(*)=O)=O 0.000 description 7
- 229910007926 ZrCl Inorganic materials 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000002524 organometallic group Chemical group 0.000 description 6
- 229910052723 transition metal Inorganic materials 0.000 description 6
- 150000003624 transition metals Chemical class 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 229910000080 stannane Inorganic materials 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 125000002091 cationic group Chemical group 0.000 description 4
- 238000006317 isomerization reaction Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000007246 mechanism Effects 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 4
- 241001120493 Arene Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 239000012300 argon atmosphere Substances 0.000 description 3
- 150000001540 azides Chemical class 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- 150000003456 sulfonamides Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000819038 Chichester Species 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 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 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 239000012041 precatalyst Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000006894 reductive elimination reaction Methods 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
- AWRJQBWBMFGDRO-XXXPIDQRSA-N (4E)-2-tributylstannylnona-2,4-dien-1-ol Chemical compound C(CCC)[Sn](C(CO)=C/C=C/CCCC)(CCCC)CCCC AWRJQBWBMFGDRO-XXXPIDQRSA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- UVAQKPFTHOACRA-UHFFFAOYSA-N (E)-2-tributylstannylhex-2-enoic acid Chemical compound CCCC[Sn](CCCC)(CCCC)C(=C/CCC)C(O)=O UVAQKPFTHOACRA-UHFFFAOYSA-N 0.000 description 1
- DAUVGYFIIADWEG-UHFFFAOYSA-N (Z)-3-tributylstannylpent-3-en-2-ol Chemical compound C(CCC)[Sn](C(C(C)O)=C/C)(CCCC)CCCC DAUVGYFIIADWEG-UHFFFAOYSA-N 0.000 description 1
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
- 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 125000005940 1,4-dioxanyl group Chemical group 0.000 description 1
- HDSBHXKJKOOYSD-UHFFFAOYSA-N 1-(1-tributylstannylprop-1-enyl)cyclohexan-1-ol Chemical compound C(CCC)[Sn](C(=C/C)C1(CCCCC1)O)(CCCC)CCCC HDSBHXKJKOOYSD-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- MUESUIRRIVMHRM-UHFFFAOYSA-N 2-tributylstannylpent-2-en-1-ol Chemical compound CCCC[Sn](CCCC)(CCCC)C(\CO)=C\CC MUESUIRRIVMHRM-UHFFFAOYSA-N 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- FHOJFWDOVXFRTN-UHFFFAOYSA-N 3-methyl-4-tributylstannylnon-4-en-2-ol Chemical compound CCCCC=C(C(C)C(C)O)[Sn](CCCC)(CCCC)CCCC FHOJFWDOVXFRTN-UHFFFAOYSA-N 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- SDCKYMIVGNCMPH-UHFFFAOYSA-N 3-tributylstannylhex-3-en-2-ol Chemical compound C(CCC)[Sn](C(C(C)O)=C/CC)(CCCC)CCCC SDCKYMIVGNCMPH-UHFFFAOYSA-N 0.000 description 1
- FJAAJVQAFJYYEJ-UHFFFAOYSA-N 3-tributylstannylocta-2,7-dien-4-ol Chemical compound C(CCC)[Sn](C(=C/C)C(CCC=C)O)(CCCC)CCCC FJAAJVQAFJYYEJ-UHFFFAOYSA-N 0.000 description 1
- MXUVBXHVXDJONI-UHFFFAOYSA-N 3-tributylstannylpent-3-en-1-ol Chemical compound CCCC[Sn](CCCC)(CCCC)C(CCO)=CC MXUVBXHVXDJONI-UHFFFAOYSA-N 0.000 description 1
- OAGZNMLKBYNNDF-UHFFFAOYSA-N 4-phenyl-3-tributylstannylbut-3-en-2-ol Chemical compound C1(=CC=CC=C1)C=C(C(C)O)/[Sn](CCCC)(CCCC)CCCC OAGZNMLKBYNNDF-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
- HVWARXDDCHCTGM-UHFFFAOYSA-N 4-tributylstannyl-4-trimethylsilylbut-3-en-1-ol Chemical compound CCCC[Sn](CCCC)(CCCC)C(=C/CCO)\[Si](C)(C)C HVWARXDDCHCTGM-UHFFFAOYSA-N 0.000 description 1
- 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 description 1
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
- WHRQBQGMEHPSLL-UHFFFAOYSA-N 9-tributylstannyloctadec-9-ene-2,17-dione Chemical compound C(CCC)[Sn](C(CCCCCCC(C)=O)=C/CCCCCCC(C)=O)(CCCC)CCCC WHRQBQGMEHPSLL-UHFFFAOYSA-N 0.000 description 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
- YUGKXLLFXWQRDQ-UHFFFAOYSA-N C(CCC)[Sn](C(=C/C)C(CCC=C/CCCCC)O)(CCCC)CCCC Chemical compound C(CCC)[Sn](C(=C/C)C(CCC=C/CCCCC)O)(CCCC)CCCC YUGKXLLFXWQRDQ-UHFFFAOYSA-N 0.000 description 1
- MFIUNBJFGJJZRI-UHFFFAOYSA-N C(CCC)[Sn](\C(=C/CCCC)\C1C(CCC1)O)(CCCC)CCCC Chemical compound C(CCC)[Sn](\C(=C/CCCC)\C1C(CCC1)O)(CCCC)CCCC MFIUNBJFGJJZRI-UHFFFAOYSA-N 0.000 description 1
- MTCVPHNWWSQSBY-UHFFFAOYSA-N C(CCC)[Sn](\C(\CCNC(C)=O)=C/C)(CCCC)CCCC Chemical compound C(CCC)[Sn](\C(\CCNC(C)=O)=C/C)(CCCC)CCCC MTCVPHNWWSQSBY-UHFFFAOYSA-N 0.000 description 1
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- QQTJMIFFFJQJKT-UHFFFAOYSA-N CC(CCCCCC=CCCC)=O Chemical compound CC(CCCCCC=CCCC)=O QQTJMIFFFJQJKT-UHFFFAOYSA-N 0.000 description 1
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- AUXDNIJIEQOXDH-UHFFFAOYSA-N CCCC[Sn](CCCC)(CCCC)C(CCCO)=C/C Chemical compound CCCC[Sn](CCCC)(CCCC)C(CCCO)=C/C AUXDNIJIEQOXDH-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- QODDPBHBZKLWPA-UHFFFAOYSA-N Cl/C(=C/CCC[Si](CC)(CC)CC)/[Sn](CCCC)(CCCC)CCCC Chemical compound Cl/C(=C/CCC[Si](CC)(CC)CC)/[Sn](CCCC)(CCCC)CCCC QODDPBHBZKLWPA-UHFFFAOYSA-N 0.000 description 1
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- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 229910020328 SiSn Inorganic materials 0.000 description 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 1
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- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
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- 230000000903 blocking effect Effects 0.000 description 1
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- 238000004364 calculation method Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000011951 cationic catalyst Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000008406 cosmetic ingredient Substances 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- JWBQJUFCNOLNNC-UHFFFAOYSA-N dec-5-yne Chemical compound CCCCC#CCCCC JWBQJUFCNOLNNC-UHFFFAOYSA-N 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical class C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940000406 drug candidate Drugs 0.000 description 1
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000010656 hydrometalation reaction Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- UIDWHMKSOZZDAV-UHFFFAOYSA-N lithium tin Chemical group [Li].[Sn] UIDWHMKSOZZDAV-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 1
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 238000006464 oxidative addition reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- HJFRLXPEVRXBQZ-UHFFFAOYSA-N pent-3-yn-2-ol Chemical compound CC#CC(C)O HJFRLXPEVRXBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical class OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 238000005797 stannylation reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- WQQFCOXXRPGJSD-UHFFFAOYSA-N tributyl-[1-(1H-indol-2-yl)dec-1-enyl]stannane Chemical compound C(CCC)[Sn](C(=C/CCCCCCCC)C=1NC2=CC=CC=C2C1)(CCCC)CCCC WQQFCOXXRPGJSD-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- SUNNZUHEMWXRMH-UHFFFAOYSA-N trimethyl(2-tributylstannyloct-2-enyl)silane Chemical compound CCCCCC=C(C[Si](C)(C)C)[Sn](CCCC)(CCCC)CCCC SUNNZUHEMWXRMH-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
- C07F7/2208—Compounds having tin linked only to carbon, hydrogen and/or halogen
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0046—Ruthenium compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/323—Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/821—Ruthenium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13189792.8 | 2013-10-22 | ||
| EP20130189792 EP2865684A1 (en) | 2013-10-22 | 2013-10-22 | Process for the ruthenium catalyzed trans-selective hydrostannation of alkynes |
| PCT/EP2014/072068 WO2015059006A1 (en) | 2013-10-22 | 2014-10-14 | Process for the ruthenium catalyzed trans-selective hydrostannation of alkynes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016536301A JP2016536301A (ja) | 2016-11-24 |
| JP2016536301A5 JP2016536301A5 (enExample) | 2018-08-09 |
| JP6499646B2 true JP6499646B2 (ja) | 2019-04-10 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016525574A Active JP6499646B2 (ja) | 2013-10-22 | 2014-10-14 | アルキンのルテニウム触媒トランス選択的ヒドロスズ化方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9556209B2 (enExample) |
| EP (2) | EP2865684A1 (enExample) |
| JP (1) | JP6499646B2 (enExample) |
| CN (1) | CN105940007B (enExample) |
| CA (1) | CA2928148C (enExample) |
| DK (1) | DK3060571T3 (enExample) |
| ES (1) | ES2659775T3 (enExample) |
| WO (1) | WO2015059006A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3438077A1 (en) * | 2017-07-31 | 2019-02-06 | Studiengesellschaft Kohle mbH | Process for deoxyfluorination of phenols |
| CN116947915A (zh) * | 2022-04-14 | 2023-10-27 | 北京理工大学 | 一种铝氢催化的乙烯基锡烷化合物的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0826047B2 (ja) * | 1994-03-22 | 1996-03-13 | 工業技術院長 | ビニルスタナン類の製造方法 |
| US20080300288A1 (en) * | 2005-06-30 | 2008-12-04 | Purdue Research Foundation | Alkenyldiarylmethanes, Fused Analogs And Syntheses Thereof |
-
2013
- 2013-10-22 EP EP20130189792 patent/EP2865684A1/en not_active Withdrawn
-
2014
- 2014-10-14 DK DK14786840.0T patent/DK3060571T3/en active
- 2014-10-14 EP EP14786840.0A patent/EP3060571B1/en active Active
- 2014-10-14 US US15/030,897 patent/US9556209B2/en not_active Expired - Fee Related
- 2014-10-14 WO PCT/EP2014/072068 patent/WO2015059006A1/en not_active Ceased
- 2014-10-14 ES ES14786840.0T patent/ES2659775T3/es active Active
- 2014-10-14 JP JP2016525574A patent/JP6499646B2/ja active Active
- 2014-10-14 CA CA2928148A patent/CA2928148C/en active Active
- 2014-10-14 CN CN201480065456.4A patent/CN105940007B/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP3060571B1 (en) | 2017-12-06 |
| EP2865684A1 (en) | 2015-04-29 |
| CA2928148C (en) | 2020-10-13 |
| WO2015059006A1 (en) | 2015-04-30 |
| DK3060571T3 (en) | 2018-03-12 |
| JP2016536301A (ja) | 2016-11-24 |
| US9556209B2 (en) | 2017-01-31 |
| CA2928148A1 (en) | 2015-04-30 |
| ES2659775T3 (es) | 2018-03-19 |
| CN105940007B (zh) | 2019-08-09 |
| EP3060571A1 (en) | 2016-08-31 |
| US20160251382A1 (en) | 2016-09-01 |
| CN105940007A (zh) | 2016-09-14 |
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