JP5549115B2 - 反応性シリル基を有する2,2’−ビピリジン誘導体、その製造方法及び遷移金属錯体 - Google Patents
反応性シリル基を有する2,2’−ビピリジン誘導体、その製造方法及び遷移金属錯体 Download PDFInfo
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- JP5549115B2 JP5549115B2 JP2009120138A JP2009120138A JP5549115B2 JP 5549115 B2 JP5549115 B2 JP 5549115B2 JP 2009120138 A JP2009120138 A JP 2009120138A JP 2009120138 A JP2009120138 A JP 2009120138A JP 5549115 B2 JP5549115 B2 JP 5549115B2
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- bipyridine
- transition metal
- atom
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- 229910052723 transition metal Inorganic materials 0.000 title claims description 62
- 150000003624 transition metals Chemical class 0.000 title claims description 61
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical class N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 title claims description 45
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 title claims description 30
- 238000000034 method Methods 0.000 title description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 43
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 229910052707 ruthenium Inorganic materials 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 239000003446 ligand Substances 0.000 claims description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 229910052762 osmium Inorganic materials 0.000 claims description 11
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 11
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- 229910052697 platinum Inorganic materials 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 7
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 7
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate group Chemical group [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229910052703 rhodium Inorganic materials 0.000 claims description 6
- 239000010948 rhodium Substances 0.000 claims description 6
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 6
- 229910052741 iridium Inorganic materials 0.000 claims description 5
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 150000003377 silicon compounds Chemical class 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- NONOKGVFTBWRLD-UHFFFAOYSA-N thioisocyanate group Chemical group S(N=C=O)N=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 claims description 3
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- -1 Phenyloxy group Chemical group 0.000 description 151
- 238000006243 chemical reaction Methods 0.000 description 26
- 229910052751 metal Inorganic materials 0.000 description 26
- 239000002184 metal Substances 0.000 description 26
- 150000001875 compounds Chemical class 0.000 description 24
- 239000000758 substrate Substances 0.000 description 21
- 229910052742 iron Inorganic materials 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 150000002430 hydrocarbons Chemical group 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000007788 liquid Substances 0.000 description 11
- 241000191368 Chlorobi Species 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 239000000523 sample Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- SJDWHBSGSYSNSV-UHFFFAOYSA-N N1=CC([SiH](C)C)=CC=C1C1=CC=CC=N1 Chemical compound N1=CC([SiH](C)C)=CC=C1C1=CC=CC=N1 SJDWHBSGSYSNSV-UHFFFAOYSA-N 0.000 description 6
- QYVILUAEULTUHM-UHFFFAOYSA-N OC=1C=C(C(=NC1)C1=NC=CC=C1)[SiH](C(C)C)C(C)C Chemical compound OC=1C=C(C(=NC1)C1=NC=CC=C1)[SiH](C(C)C)C(C)C QYVILUAEULTUHM-UHFFFAOYSA-N 0.000 description 6
- 239000012491 analyte Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000010409 thin film Substances 0.000 description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- AWJPULCSDFBFDR-UHFFFAOYSA-N 5-bromo-2-pyridin-2-ylpyridine Chemical compound N1=CC(Br)=CC=C1C1=CC=CC=N1 AWJPULCSDFBFDR-UHFFFAOYSA-N 0.000 description 5
- AARXRNMNAHTWST-UHFFFAOYSA-N N1=CC([SiH](C(C)C)C(C)C)=CC=C1C1=CC=CC=N1 Chemical compound N1=CC([SiH](C(C)C)C(C)C)=CC=C1C1=CC=CC=N1 AARXRNMNAHTWST-UHFFFAOYSA-N 0.000 description 5
- QUDGQDJJDPGOQE-UHFFFAOYSA-N [SiH3]c1cccnc1-c1ccccn1 Chemical compound [SiH3]c1cccnc1-c1ccccn1 QUDGQDJJDPGOQE-UHFFFAOYSA-N 0.000 description 5
- 239000004065 semiconductor Substances 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 108020004414 DNA Proteins 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229910017052 cobalt Inorganic materials 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- 150000004696 coordination complex Chemical class 0.000 description 4
- 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 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 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 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 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 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
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- 238000002360 preparation method Methods 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 125000006850 spacer group Chemical group 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- 238000001269 time-of-flight mass spectrometry Methods 0.000 description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XNTDTCVKWPYEKU-UHFFFAOYSA-N CC(=C[SiH2]C=1C=CC(=NC1)C1=NC=CC=C1)C Chemical compound CC(=C[SiH2]C=1C=CC(=NC1)C1=NC=CC=C1)C XNTDTCVKWPYEKU-UHFFFAOYSA-N 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- 102000053602 DNA Human genes 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000012327 Ruthenium complex Substances 0.000 description 3
- 108020004682 Single-Stranded DNA Proteins 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
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- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
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- 102000004169 proteins and genes Human genes 0.000 description 3
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- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 3
- 229910001887 tin oxide Inorganic materials 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- ZTWIEIFKPFJRLV-UHFFFAOYSA-K trichlororuthenium;trihydrate Chemical compound O.O.O.Cl[Ru](Cl)Cl ZTWIEIFKPFJRLV-UHFFFAOYSA-K 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- JNWPRPLNUUMYCM-UHFFFAOYSA-N 5-bromo-2-(5-bromopyridin-2-yl)pyridine Chemical compound N1=CC(Br)=CC=C1C1=CC=C(Br)C=N1 JNWPRPLNUUMYCM-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- MCYPISDDNSRIMG-UHFFFAOYSA-N ClC=1C=C(C(=NC=1)C1=NC=CC=C1)[SiH](C(C)C)C(C)C Chemical compound ClC=1C=C(C(=NC=1)C1=NC=CC=C1)[SiH](C(C)C)C(C)C MCYPISDDNSRIMG-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
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- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- IGSUJBNDAWQLST-UHFFFAOYSA-N chloro-di(propan-2-yl)silicon Chemical compound CC(C)[Si](Cl)C(C)C IGSUJBNDAWQLST-UHFFFAOYSA-N 0.000 description 2
- XSDCTSITJJJDPY-UHFFFAOYSA-N chloro-ethenyl-dimethylsilane Chemical compound C[Si](C)(Cl)C=C XSDCTSITJJJDPY-UHFFFAOYSA-N 0.000 description 2
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- 239000010949 copper Substances 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 2
- WEAFESPXUBTSGL-UHFFFAOYSA-N diethyl(hydroxy)silane Chemical group CC[SiH](O)CC WEAFESPXUBTSGL-UHFFFAOYSA-N 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
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- LWIGVRDDANOFTD-UHFFFAOYSA-N hydroxy(dimethyl)silane Chemical group C[SiH](C)O LWIGVRDDANOFTD-UHFFFAOYSA-N 0.000 description 2
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
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- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
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- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 2
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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- 239000010936 titanium Substances 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- SITPFIOORHQBOO-UHFFFAOYSA-N triethoxy-(6-pyridin-2-ylpyridin-3-yl)silane Chemical compound N1=CC([Si](OCC)(OCC)OCC)=CC=C1C1=CC=CC=N1 SITPFIOORHQBOO-UHFFFAOYSA-N 0.000 description 2
- 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 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
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- 150000007514 bases Chemical class 0.000 description 1
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- SUDHVXIPIDQEIT-UHFFFAOYSA-N bis(1,1,2,2,2-pentafluoroethylsulfonyl)azanide;1-ethyl-3-methylimidazol-3-ium Chemical compound CCN1C=C[N+](C)=C1.FC(F)(F)C(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)C(F)(F)F SUDHVXIPIDQEIT-UHFFFAOYSA-N 0.000 description 1
- INDFXCHYORWHLQ-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1-butyl-3-methylimidazol-3-ium Chemical compound CCCCN1C=C[N+](C)=C1.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F INDFXCHYORWHLQ-UHFFFAOYSA-N 0.000 description 1
- LUWJQOLQUXTUGM-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)methylsulfonyl-trifluoromethane;1,2-dimethyl-3-propylimidazol-1-ium Chemical compound CCCN1C=C[N+](C)=C1C.FC(F)(F)S(=O)(=O)[C-](S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F LUWJQOLQUXTUGM-UHFFFAOYSA-N 0.000 description 1
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- ZUKYLGDWMRLIKI-UHFFFAOYSA-N chloro-ethyl-methylsilicon Chemical compound CC[Si](C)Cl ZUKYLGDWMRLIKI-UHFFFAOYSA-N 0.000 description 1
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- BYYBKLIBZQWDDP-UHFFFAOYSA-N copper;(4,5-dichloro-6-pyridin-2-ylpyridin-3-yl)-triethoxysilane Chemical compound [Cu].ClC1=C(Cl)C([Si](OCC)(OCC)OCC)=CN=C1C1=CC=CC=N1 BYYBKLIBZQWDDP-UHFFFAOYSA-N 0.000 description 1
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- 125000002704 decyl 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])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 238000001514 detection method Methods 0.000 description 1
- CDKMZLBYRVHTDQ-UHFFFAOYSA-N di(propan-2-yl)-(4,5,6-trichloro-2-pyridin-2-ylpyridin-3-yl)silane Chemical compound ClC1=C(C(=C(C(=N1)C1=NC=CC=C1)[SiH](C(C)C)C(C)C)Cl)Cl CDKMZLBYRVHTDQ-UHFFFAOYSA-N 0.000 description 1
- JAONJTDQXUSBGG-UHFFFAOYSA-N dialuminum;dizinc;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Al+3].[Al+3].[Zn+2].[Zn+2] JAONJTDQXUSBGG-UHFFFAOYSA-N 0.000 description 1
- GSENNYNYEKCQGA-UHFFFAOYSA-N dichloro-di(propan-2-yl)silane Chemical compound CC(C)[Si](Cl)(Cl)C(C)C GSENNYNYEKCQGA-UHFFFAOYSA-N 0.000 description 1
- 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
- 150000001993 dienes Chemical class 0.000 description 1
- ZMAPKOCENOWQRE-UHFFFAOYSA-N diethoxy(diethyl)silane Chemical compound CCO[Si](CC)(CC)OCC ZMAPKOCENOWQRE-UHFFFAOYSA-N 0.000 description 1
- IUOMUWMJCPVKGH-UHFFFAOYSA-N diethyl-hydroxy-(6-pyridin-2-ylpyridin-3-yl)silane Chemical compound N1=CC([Si](O)(CC)CC)=CC=C1C1=CC=CC=N1 IUOMUWMJCPVKGH-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- UMHVWCBTMADILL-UHFFFAOYSA-N dihexyl-hydroxy-(6-pyridin-2-ylpyridin-3-yl)silane Chemical compound N1=CC([Si](O)(CCCCCC)CCCCCC)=CC=C1C1=CC=CC=N1 UMHVWCBTMADILL-UHFFFAOYSA-N 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 1
- VHPUZTHRFWIGAW-UHFFFAOYSA-N dimethoxy-di(propan-2-yl)silane Chemical compound CO[Si](OC)(C(C)C)C(C)C VHPUZTHRFWIGAW-UHFFFAOYSA-N 0.000 description 1
- AKRYJDIBAUYHTR-UHFFFAOYSA-N dimethyl-(6-pyridin-2-ylpyridin-3-yl)silane iron Chemical compound [Fe].N1=CC([SiH](C)C)=CC=C1C1=CC=CC=N1.N1=CC([SiH](C)C)=CC=C1C1=CC=CC=N1 AKRYJDIBAUYHTR-UHFFFAOYSA-N 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
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- KDXPGTUMUQRMPD-UHFFFAOYSA-N ethane-1,2-diamine nickel(2+) Chemical compound [Ni+2].NCCN KDXPGTUMUQRMPD-UHFFFAOYSA-N 0.000 description 1
- CVYJFILCQXLQFK-UHFFFAOYSA-N ethoxy-[6-[5-[ethoxy(dimethyl)silyl]pyridin-2-yl]pyridin-3-yl]-dimethylsilane Chemical compound N1=CC([Si](C)(C)OCC)=CC=C1C1=CC=C([Si](C)(C)OCC)C=N1 CVYJFILCQXLQFK-UHFFFAOYSA-N 0.000 description 1
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- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- 239000010931 gold Substances 0.000 description 1
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- ZJYYHGLJYGJLLN-UHFFFAOYSA-N guanidinium thiocyanate Chemical compound SC#N.NC(N)=N ZJYYHGLJYGJLLN-UHFFFAOYSA-N 0.000 description 1
- OAUPFOAQTNNXJX-UHFFFAOYSA-N hydroxy-[6-[5-[hydroxy(dimethyl)silyl]pyridin-2-yl]pyridin-3-yl]-dimethylsilane Chemical compound N1=CC([Si](C)(O)C)=CC=C1C1=CC=C([Si](C)(C)O)C=N1 OAUPFOAQTNNXJX-UHFFFAOYSA-N 0.000 description 1
- AAAACYXVDNAANB-UHFFFAOYSA-N hydroxy-di(propan-2-yl)-(2-pyridin-2-ylpyridin-3-yl)silane Chemical compound O[Si](C(C)C)(C(C)C)C=1C(=NC=CC=1)C1=NC=CC=C1 AAAACYXVDNAANB-UHFFFAOYSA-N 0.000 description 1
- QJJVIJRDXFSXLI-UHFFFAOYSA-N hydroxy-di(propan-2-yl)-(6-pyridin-2-ylpyridin-3-yl)silane Chemical compound N1=CC([Si](O)(C(C)C)C(C)C)=CC=C1C1=CC=CC=N1 QJJVIJRDXFSXLI-UHFFFAOYSA-N 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229920000554 ionomer Polymers 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052744 lithium 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
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-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
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- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- CNFDGXZLMLFIJV-UHFFFAOYSA-L manganese(II) chloride tetrahydrate Chemical compound O.O.O.O.[Cl-].[Cl-].[Mn+2] CNFDGXZLMLFIJV-UHFFFAOYSA-L 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
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- 239000000203 mixture Substances 0.000 description 1
- 238000004776 molecular orbital Methods 0.000 description 1
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- 230000007935 neutral effect Effects 0.000 description 1
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- 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
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
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- 229920002223 polystyrene Polymers 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003303 ruthenium Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
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- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 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
- HBYCZEOYOCONCV-UHFFFAOYSA-N tert-butyl(dichloro)silane Chemical compound CC(C)(C)[SiH](Cl)Cl HBYCZEOYOCONCV-UHFFFAOYSA-N 0.000 description 1
- TWRVYXVQOJCHIF-UHFFFAOYSA-N tert-butyl-chloro-methylsilane Chemical compound C[SiH](Cl)C(C)(C)C TWRVYXVQOJCHIF-UHFFFAOYSA-N 0.000 description 1
- FBEIPJNQGITEBL-UHFFFAOYSA-J tetrachloroplatinum Chemical compound Cl[Pt](Cl)(Cl)Cl FBEIPJNQGITEBL-UHFFFAOYSA-J 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-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
- WJVLFZPLIQQRNT-UHFFFAOYSA-N triethoxy-[6-(5-triethoxysilylpyridin-2-yl)pyridin-3-yl]silane Chemical compound N1=CC([Si](OCC)(OCC)OCC)=CC=C1C1=CC=C([Si](OCC)(OCC)OCC)C=N1 WJVLFZPLIQQRNT-UHFFFAOYSA-N 0.000 description 1
- JFZKOODUSFUFIZ-UHFFFAOYSA-N trifluoro phosphate Chemical compound FOP(=O)(OF)OF JFZKOODUSFUFIZ-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Images
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 System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0896—Compounds with a Si-H linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
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Description
[1]
下記一般式(1)で表される反応性シリル基を有する2,2’−ビピリジン誘導体。
(式中、R1、R2はそれぞれ独立にハロゲン原子置換又は非置換の炭素数1〜10のアルキル基を表す。R3はハロゲン原子置換又は非置換の炭素数2〜10のアルケニル基、水酸基、又は水素原子を表す。R4 は水素原子を表し、R5、R6、R7、R8 はそれぞれ水素原子を表す。)
[2]
上記一般式(1)において、R1及びR2がメチル基又はイソプロピル基である[1]記載の反応性シリル基を有する2,2’−ビピリジン誘導体。
[3]
下記一般式(2)で表される5−ハロ−2,2’−ビピリジン誘導体から生成させた5−メタロ−2,2’−ビピリジン誘導体と、下記一般式(3)で表されるケイ素化合物を反応させることによる[1]記載の一般式(1)において、R4 が水素原子であり、R3がハロゲン原子置換又は非置換の炭素数2〜10のアルケニル基、水酸基、又は水素原子である反応性シリル基を有する2,2’−ビピリジン誘導体の製造方法。
(式中、Halは塩素原子、臭素原子、又はヨウ素原子を表し、R4a は水素原子、R5、R6、R7、R8は請求項1記載の式(1)で定義したものと同じ置換基を表す。)
XSiR1R2R3a (3)
(式中、Xはハロゲン原子、又は炭素数1〜10のアルコキシ基、アルケニロキシ基、アリーロキシ基もしくはアラルキルオキシ基を表し、R1、R2は式(1)で定義したものと同じ置換基を表す。R3aはハロゲン原子置換又は非置換の炭素数2〜10のアルケニル基、水酸基、又は水素原子である。)
[4]
[1]又は[2]記載の反応性シリル基を有する2,2’−ビピリジン誘導体を少なくとも一つ配位子として有する遷移金属錯体。
[5]
遷移金属が、ルテニウム、オスミウム、ロジウム、イリジウム、パラジウム、白金の中から選ばれる[4]記載の遷移金属錯体。
[6]
下記一般式(5)で表される[4]記載の遷移金属錯体。
(X)mM(L1)n(L2)p (5)
[式中、Mはルテニウム、オスミウム、ロジウム、イリジウム、パラジウム、白金から選ばれる遷移金属である。mは0〜3の整数であり、Xはハロゲン原子、チオシアナート基、チオイソシアナート基、水酸基、シアノ基、シアナート基、イソシアナート基、カルボニル基の中から独立して選択される。nは1〜3の整数であり、L1は[1]記載の一般式(1)で表される反応性シリル基を有する2,2’−ビピリジン誘導体を表す。pは0〜2の整数であり、L2は下記一般式(6)
(式中、R9、R10、R11、R12、R13、R14、R15、R16は同一でも異なってもよく、それぞれハロゲン原子置換又は非置換の炭素数1〜20の1価炭化水素基又は水素原子を表す。但し、n+pは1〜3の整数である。)
で表される2,2’−ビピリジン誘導体を示す。]
[7]
担持型遷移金属触媒用である[4]〜[6]のいずれかに記載の遷移金属錯体。
XSiR1R2R3 (3)
XSiR1R2R3 (3)
(X)mM(L1)n(L2)p (5)
(式中、R9、R10、R11、R12、R13、R14、R15、R16は同一でも異なってもよく、それぞれ置換又は非置換の炭素数1〜20の1価炭化水素基又は水素原子を表す。但し、n+pは1〜3の整数である。)
ジヒドロキシビス(5−トリエトキシシリル−2,2’−ビピリジン)鉄、ジヒドロキシビス(5−ジメチルシリル−2,2’−ビピリジン)鉄、ジヒドロキシビス(5−ジイソプロピルシリル−2,2’−ビピリジン)鉄、ジヒドロキシビス(5−ジイソブチルシリル−2,2’−ビピリジン)鉄、ジヒドロキシビス(5−クロロジイソプロピルシリル−2,2’−ビピリジン)鉄、ジヒドロキシビス(5−ヒドロキシジイソプロピルシリル−2,2’−ビピリジン)鉄、ジヒドロキシビス(5−ヒドロキシジエチルシリル−2,2’−ビピリジン)鉄、ジクロロビス(5,5’−ビス(トリエトキシシリル)−2,2’−ビピリジン)鉄、ジクロロビス(5,5’−ビス(クロロジイソプロピルシリル)−2,2’−ビピリジン)鉄、ジクロロビス(5,5’−ビス(ヒドロキシジイソプロピルシリル)−2,2’−ビピリジン)鉄、ジクロロビス(5,5’−ビス(ヒドロキシジエチルシリル)−2,2’−ビピリジン)鉄、ジクロロビス(5−ヒドロキシジイソプロピルシリル−5’−ジメチルビニルシリル−2,2’−ビピリジン)鉄、ジクロロビス(5−トリエトキシシリル−2,2’−ビピリジン)オスミウム、ジクロロビス(5−クロロジイソプロピルシリル−2,2’−ビピリジン)オスミウム、ジクロロビス(5−ヒドロキシジイソプロピルシリル−2,2’−ビピリジン)オスミウム、ジクロロビス(5−ヒドロキシジエチルシリル−2,2’−ビピリジン)オスミウム、ジクロロビス(5,5’−トリエトキシシリル−2,2’−ビピリジン)オスミウム、ジクロロビス(5,5’−クロロジイソプロピルシリル−2,2’−ビピリジン)オスミウム、ジクロロビス(5,5’−ヒドロキシジイソプロピルシリル−2,2’−ビピリジン)オスミウム、ジクロロビス(5,5’−ヒドロキシジエチルシリル−2,2’−ビピリジン)オスミウム、ジクロロビス(5−トリエトキシシリル−2,2’−ビピリジン)コバルト、ジクロロビス(5−クロロジイソプロピルシリル−2,2’−ビピリジン)コバルト、ジクロロビス(5−ヒドロキシジイソプロピルシリル−2,2’−ビピリジン)コバルト、ジクロロビス(5−ヒドロキシジエチルシリル−2,2’−ビピリジン)コバルト、ジクロロビス(5,5’−ビス(トリエトキシシリル)−2,2’−ビピリジン)コバルト、(5,5’−ビス(クロロジイソプロピルシリル)−2,2’−ビピリジン)コバルト、ジクロロビス(5,5’−ビス(ヒドロキシジイソプロピルシリル)−2,2’−ビピリジン)コバルト、ジクロロビス(5,5’−ビス(ヒドロキシジエチルシリル)−2,2’−ビピリジン)コバルト、クロロビス(5−トリエトキシシリル−2,2’−ビピリジン)イリジウム、クロロビス(5−クロロジイソプロピルシリル−2,2’−ビピリジン)イリジウム、クロロビス(5−ヒドロキシジイソプロピルシリル−2,2’−ビピリジン)イリジウム、ジクロロ(5−トリエトキシシリル−2,2’−ビピリジン)パラジウム、ジクロロ(5−クロロジイソプロピルシリル−2,2’−ビピリジン)パラジウム、ジクロロ(5−ヒドロキシジイソプロピルシリル−2,2’−ビピリジン)パラジウム、クロロビス(5−トリエトキシシリル−2,2’−ビピリジン)ロジウム、クロロビス(5−クロロジイソプロピルシリル−2,2’−ビピリジン)ロジウム、クロロビス(5−ヒドロキシジイソプロピルシリル−2,2’−ビピリジン)ロジウム、ジクロロ(5−トリエトキシシリル−2,2’−ビピリジン)ニッケル、ジクロロ(5−クロロジイソプロピルシリル−2,2’−ビピリジン)ニッケル、ジクロロ(5−ヒドロキシジイソプロピルシリル−2,2’−ビピリジン)ニッケル、ジクロロ(5−トリエトキシシリル−2,2’−ビピリジン)銅、ジクロロ(5−クロロジイソプロピルシリル−2,2’−ビピリジン)銅、ジクロロ(5−ヒドロキシジイソプロピルシリル−2,2’−ビピリジン)銅、ジクロロ(5−トリエトキシシリル−2,2’−ビピリジン)白金、ジクロロ(5−クロロジイソプロピルシリル−2,2’−ビピリジン)白金、ジクロロ(5−ヒドロキシジイソプロピルシリル−2,2’−ビピリジン)白金、ジクロロビス(5−ヒドロキシジイソプロピルシリル−2,2’−ビピリジン)(4,4’−ジノナニル−2,2’−ビピリジン)ルテニウム、ジクロロビス(5−ヒドロキシジイソプロピルシリル−2,2’−ビピリジン)(2−(4−ヘキシロキシ)−スチリル−2,2’−ビピリジン)ルテニウム、ジクロロビス(5−ヒドロキシジイソプロピルシリル−2,2’−ビピリジン)((4−メトキシ)−スチリル−2,2’−ビピリジン)ルテニウム、ジクロロビス(5−ヒドロキシジイソプロピルシリル−2,2’−ビピリジン)(2−(4−tert−ブトキシ)−スチリル−2,2’−ビピリジン)ルテニウム、ジクロロビス(5−ヒドロキシジイソプロピルシリル−2,2’−ビピリジン)(5−へキシルチオフェン−2−イル−スチリル−2,2’−ビピリジン)ルテニウム、ジチオシアナトビス(5−ヒドロキシジイソプロピルシリル−2,2’−ビピリジン)(4,4’−ジノナニル−2,2’−ビピリジン)ルテニウム、ジチオシアナトビス(5−ヒドロキシジイソプロピルシリル−2,2’−ビピリジン)(2−(4−ヘキシロキシ)−スチリル−2,2’−ビピリジン)ルテニウム、ジチオシアナトビス(5−ヒドロキシジイソプロピルシリル−2,2’−ビピリジン)((4−メトキシ)−スチリル−2,2’−ビピリジン)ルテニウム、ジチオシアナトビス(5−ヒドロキシジイソプロピルシリル−2,2’−ビピリジン)(2−(4−tert−ブトキシ)−スチリル−2,2’−ビピリジン)ルテニウム、ジチオシアナトビス(5−ヒドロキシジイソプロピルシリル−2,2’−ビピリジン)(5−へキシルチオフェン−2−イル−スチリル−2,2’−ビピリジン)ルテニウム等が挙げられる。
一般式(5)中p=0の場合、下記反応式で示すように一般式(1)で表される2,2’−ビピリジン誘導体と(X)mMで表される金属塩を反応させることにより得られる。(X)mMで表される金属塩の例としては、塩化マンガン・四水和物、塩化鉄(III)、塩化ルテニウム・三水和物、塩化オスミウム・三水和物、塩化コバルト(III)、塩化ロジウム・三水和物、三塩化イリジウム、塩化パラジウム(II)、塩化ニッケル・六水和物、塩化白金(IV)、塩化銅(II)等が挙げられる。
上記反応式中、M、X、L1、L2、m、n、p及びqは、上記一般式(5)において説明したとおりである。qは1〜6の整数であり、Lは中性配位子を表し、例えばジメチルスルホキシド、p−シメン、トリフェニルホスフィン、シクロオクタジエン、エチレンジアミン等が挙げられる。なお、(X)mM(L)qで表される遷移金属錯体にL1、L2を順不同で順次加えてもよく、(X)mM(L)q、L1及びL2を一括で反応させてもよい。
100mlの3つ口フラスコに還流冷却器、撹拌機を取り付け、内部を窒素置換した。このフラスコに5−ブロモビピリジン718.8mg(3.07mmol)と脱水ジエチルエーテル20mlを仕込んだ。その後、ドライアイスバスで−70℃まで冷やし、2.73Mのn−ブチルリチウム2.0ml(5.46mmol)を約10分かけて滴下した。そのままの温度で30分撹拌した後、ジメチルビニルクロロシラン750.0mg(6.21mmol)を加え、徐々に室温まで昇温させ、終夜で撹拌を行った。水を加えて反応を終了した後、分液操作により有機層を抽出した。得られた溶液を硫酸マグネシウムにより乾燥し、ロータリーエバポレーターにて減圧濃縮した後、HPLCにより精製して黄色液体552.2mgを得た。この液体のNMRスペクトル及びGC−MSスペクトルを測定した結果、5−ジメチルビニルシリル−2,2’−ビピリジンであることが確認された。収率は74.9%であった。以下にその結果を示す。
1H−NMR(300MHz,δ in CDCl3):0.41(s,6H),5.81(dd,J=20.0Hz,3.8Hz,1H),6.12(dd,J=14.7Hz,J=3.8Hz,1H),6.30(dd,J=20.0Hz,14.7Hz,1H),7.30(ddd,J=7.5Hz,J=4.8Hz,J=1.2Hz,1H),7.81(dd,J=7.7Hz,J=1.9Hz,1H),7.93(dd,J=7.8Hz,J=1.8Hz,1H),8.36(dd,J=7.8Hz,J=0.9Hz,1H),8.41(dt,J=7.9Hz,J=1.0Hz,1H),8.69(ddd,J=4.8Hz,J=1.8Hz,J=0.9Hz,1H),8.76(dd,J=1.7Hz,J=1.0Hz,1H)
13C−NMR(75MHz,δ in CDCl3):−3.06,120.28,121.11,123.77,133.41,133.81,136.75,136.90,142.62,149.22,153.82,156.25,156.32
GC−MS(EI)m/z:240(M+),225(M+−Me),213,199
100mlの3つ口フラスコに還流冷却器、撹拌機を取り付け、内部を窒素置換した。このフラスコに5−ブロモビピリジン234.0mg(1.0mmol)と脱水ジエチルエーテル7mlを仕込んだ。その後、ドライアイスバスで−70℃まで冷やし、1.58Mのn−ブチルリチウム0.7ml(1.1mmol)を約10分かけて滴下した。そのままの温度で30分撹拌した後、ジメチルクロロシラン0.16ml(1.47mmol)を加え、徐々に室温まで昇温させ、終夜で撹拌を行った。水を加えて反応を終了した後、分液操作により有機層を抽出した。得られた溶液を硫酸マグネシウムにより乾燥し、ロータリーエバポレーターにて減圧濃縮し、HPLCにより精製して無色液体163.4mgを得た。この液体のNMRスペクトル及びGC−MSスペクトルを測定した結果、5−ジメチルシリル−2,2’−ビピリジンであることが確認された。収率は76.4%であった。以下にその結果を示す。
1H−NMR(300MHz,δ in CDCl3):0.41(d,J=3.8Hz,6H),4.51(sept,J=7.6Hz,J=4.9Hz,J=1.2Hz,1H),7.31(ddd,J=7.5Hz,J=4.8Hz,J=1.2Hz,1H),7.81(ddd,J=8.0Hz,J=7.6Hz,J=1.7Hz,1H),7.95(dd,J=7.8Hz,J=1.8Hz,1H),8.37(dd,J=7.8Hz,J=1.0Hz,1H),8.42(dt,J=7.8Hz,J=1.2Hz,1.0Hz,1H),8.69(ddd,J=4.8Hz,J=1.8Hz,J=0.9Hz,1H),8.76(dd,J=1.7Hz,J=1.0Hz,1H)
13C−NMR(75MHz,δ in CDCl3):−4.03,120.34,121.14,123.82,132.46,136.90,142.76,149.22,153.88,156.17,156.54
GC−MS(EI)m/z:214(M+),199(M+−Me),184(M+−Me−Me)
100mlの3つ口フラスコに還流冷却器、撹拌機を取り付け、内部を窒素置換した。このフラスコに5−ブロモビピリジン711.1mg(3.04mmol)と脱水ジエチルエーテル15mlを仕込み実施例2と同様の操作で、5−ジメチルシリル−2,2’−ビピリジンを調製した。その後、還流冷却器、温度計、及び撹拌機を取り付け、内部を窒素置換した100mlの3つ口フラスコに上記で得られた5−ジメチルシリル−2,2’−ビピリジン、5%パラジウム炭素触媒30mg及びエタノール15mlを仕込んだ。その後、内温20〜30℃で20時間撹拌した。触媒をろ過により除去後、得られたろ液をロータリーエバポレーターにて減圧濃縮した後、HPLCにより精製して黄色液体560mgを得た。この液体のNMRスペクトル及びGC−MSスペクトルを測定した結果、5−ジメチルトリエトキシシリル−2,2’−ビピリジンであることが確認された。収率は71.4%であった。以下にその結果を示す。
1H−NMR(300MHz,δ in CDCl3):0.45(s,6H),1.21(t,J=7.0Hz,6H),3.72(q,J=7.0Hz,2H),7.32(ddd,J=7.6Hz,J=4.7Hz,J=1.1Hz,1H),7.82(ddd,J=8.0Hz,J=7.6Hz,J=1.8Hz,1H),7.99(dd,J=7.8Hz,J=1.8Hz,1H),8.39(dd,7.84,J=1.8Hz),8.42(dt,J=8.0Hz,J=1.1Hz),8.69(ddd,J=4.8Hz,J=1.8Hz,J=0.8Hz,1H),8.83(dd,J=1.8Hz,J=1.0Hz,1H)
13C−NMR(75MHz,δ in CDCl3):−1.67,18.42,58.88,120.39,121.19,123.86,132.99,136.93,142.31,149.26,153.54,156.18,156.79
GC−MS(EI)m/z:258(M+),243(M+−Me),215,199,183
100mlの3つ口フラスコに還流冷却器、撹拌機を取り付け、内部を窒素置換した。このフラスコに5−ブロモビピリジン702.4mg(3.0mmol)と脱水ジエチルエーテル20mlを仕込んだ。その後、ドライアイスバスで−70℃まで冷やし、2.6Mのn−ブチルリチウム1.3ml(3.2mmol)を約10分かけて滴下した。そのままの温度で30分撹拌した後、ジイソプロピルクロロシラン1.0g(6.6mmol)を加え、徐々に室温まで昇温させ、終夜で撹拌を行った。水を加えて反応を終了した後、分液操作により有機層を抽出した。得られた溶液を硫酸マグネシウムにより乾燥し、ロータリーエバポレーターにて減圧濃縮し、HPLCにより精製して無色液体640mgを得た。この液体のNMRスペクトル及びGC−MSスペクトルを測定した結果、5−ジイソプロピルシリル−2,2’−ビピリジンであることが確認された。収率は79.0%であった。以下にその結果を示す。
1H−NMR(300MHz,δ in CDCl3):1.02(m,7H),1.09(m,7H),4.02(t,J=3.2Hz,1H),7.31(ddd,J=7.5Hz,J=4.7Hz,J=1.1Hz,1H),7.82(ddd,J=8.0Hz,J=7.6Hz,J=1.7Hz,1H),7.96(dd,J=7.8Hz,J=1.8Hz,1H),8.37(dd,J=7.8Hz,J=1.0Hz,1H),8.42(dt,J=7.8Hz,J=1.2Hz,J=1.0Hz,1H),8.69(ddd,J=4.8Hz,J=1.8Hz,J=0.9Hz,1H),8.77(dd,J=1.7Hz,J=1.0Hz,1H)
13C−NMR(75MHz,δ in CDCl3):10.50,18.36,18.57,120.29,121.11,123.83,129.57,136.93,144.24,149.26,154.91,156.21,156.51
GC−MS(EI)m/z:270(M+),227(M+−CH(CH3)2)
100mlの3つ口フラスコに還流冷却器、撹拌機を取り付け、内部を窒素置換した。このフラスコに5−ジイソプロピルシリル−2,2’−ビピリジン130.9mg、塩化ルテニウム・三水和物63.3mgとDMF8mlを仕込んだ。130℃で6時間還流した後、ロータリーエバポレーターにて減圧濃縮し得られた結晶をジエチルエーテルでろ過し、黒色の固体151.7mgを得た。この固体のMALDI−TOFMSを測定した結果Ru−ビス(5−ジイソプロピル−2,2’−ビピリジン)−ジクロライドシラノールであることが確認された。収率は84.3%であった。なお、本実施例では、錯体形成時に塩化ルテニウム・三水和物が触媒としても働き、ジイソプロピルシリル基が脱水素反応によってヒドロキシジイソプロピルシリル基に変換された。
MALDI−TOFMS m/z:744(M+)
図1にはIRスペクトルのチャートを示した。
100mlの光を遮光した3つ口フラスコに還流冷却器、撹拌機を取り付け、内部を窒素置換した。このフラスコにビス(ジクロロビス(5−ヒドロキシジイソプロピルシリル−2,2’−ビピリジン)−ルテニウム(II)117.3mgとDMF20mlを仕込んだ。これと別にチオシアン酸ナトリウム418.3mgを2mlの蒸留水に溶かし、上記の溶液に加え、6時間還流した。この操作の後、反応混合物を放冷しロータリーエバポレーターにて減圧濃縮し、水を加えて析出した固体をろ過した後、シリカゲルクロマトグラフィー(CHCl3:MeOH=9:1)による精製を行い、紫色の固体50.4mgを得た。この固体のMALDI−TOFMSを測定した結果ジチオシアナト−ビス(5−ヒドロキシジイソプロピルシリル−2,2’−ビピリジン)−ルテニウム(II)であることが確認された。収率は40.5%であった。
MALDI−TOFMS m/z:790(M+)
図2にはIRスペクトルのチャートを示した。
Claims (7)
- 上記一般式(1)において、R1及びR2がメチル基又はイソプロピル基である請求項1記載の反応性シリル基を有する2,2’−ビピリジン誘導体。
- 下記一般式(2)で表される5−ハロ−2,2’−ビピリジン誘導体から生成させた5−メタロ−2,2’−ビピリジン誘導体と、下記一般式(3)で表されるケイ素化合物を反応させることによる請求項1記載の一般式(1)において、R4 が水素原子であり、R3がハロゲン原子置換又は非置換の炭素数2〜10のアルケニル基、水酸基、又は水素原子である反応性シリル基を有する2,2’−ビピリジン誘導体の製造方法。
(式中、Halは塩素原子、臭素原子、又はヨウ素原子を表し、R4a は水素原子、R5、R6、R7、R8は請求項1記載の式(1)で定義したものと同じ置換基を表す。)
XSiR1R2R3a (3)
(式中、Xはハロゲン原子、又は炭素数1〜10のアルコキシ基、アルケニロキシ基、アリーロキシ基もしくはアラルキルオキシ基を表し、R1、R2は式(1)で定義したものと同じ置換基を表す。R3aはハロゲン原子置換又は非置換の炭素数2〜10のアルケニル基、水酸基、又は水素原子である。) - 請求項1又は2記載の反応性シリル基を有する2,2’−ビピリジン誘導体を少なくとも一つ配位子として有する遷移金属錯体。
- 遷移金属が、ルテニウム、オスミウム、ロジウム、イリジウム、パラジウム、白金の中から選ばれる請求項4記載の遷移金属錯体。
- 下記一般式(5)で表される請求項4記載の遷移金属錯体。
(X)mM(L1)n(L2)p (5)
[式中、Mはルテニウム、オスミウム、ロジウム、イリジウム、パラジウム、白金から選ばれる遷移金属である。mは0〜3の整数であり、Xはハロゲン原子、チオシアナート基、チオイソシアナート基、水酸基、シアノ基、シアナート基、イソシアナート基、カルボニル基の中から独立して選択される。nは1〜3の整数であり、L1は請求項1記載の一般式(1)で表される反応性シリル基を有する2,2’−ビピリジン誘導体を表す。pは0〜2の整数であり、L2は下記一般式(6)
(式中、R9、R10、R11、R12、R13、R14、R15、R16は同一でも異なってもよく、それぞれハロゲン原子置換又は非置換の炭素数1〜20の1価炭化水素基又は水素原子を表す。但し、n+pは1〜3の整数である。)
で表される2,2’−ビピリジン誘導体を示す。] - 担持型遷移金属触媒用である請求項4〜6のいずれか1項記載の遷移金属錯体。
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