JP7187149B2 - 地球に豊富な遷移金属フリ-触媒による芳香族複素環のシリル化 - Google Patents
地球に豊富な遷移金属フリ-触媒による芳香族複素環のシリル化 Download PDFInfo
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- JP7187149B2 JP7187149B2 JP2017506415A JP2017506415A JP7187149B2 JP 7187149 B2 JP7187149 B2 JP 7187149B2 JP 2017506415 A JP2017506415 A JP 2017506415A JP 2017506415 A JP2017506415 A JP 2017506415A JP 7187149 B2 JP7187149 B2 JP 7187149B2
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- mmol
- alkyl
- optionally substituted
- aryl
- aromatic
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- 238000006884 silylation reaction Methods 0.000 title claims description 124
- 230000007704 transition Effects 0.000 title description 5
- 238000000034 method Methods 0.000 claims description 231
- -1 substituted Chemical class 0.000 claims description 163
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 155
- 125000003118 aryl group Chemical group 0.000 claims description 145
- 239000000758 substrate Substances 0.000 claims description 119
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 116
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 91
- 125000001072 heteroaryl group Chemical group 0.000 claims description 70
- 125000000217 alkyl group Chemical group 0.000 claims description 68
- 238000010438 heat treatment Methods 0.000 claims description 57
- 239000000203 mixture Substances 0.000 claims description 47
- 229910052760 oxygen Inorganic materials 0.000 claims description 40
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 38
- 125000001424 substituent group Chemical group 0.000 claims description 34
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 32
- 229910052799 carbon Inorganic materials 0.000 claims description 31
- 239000003054 catalyst Substances 0.000 claims description 29
- 230000015572 biosynthetic process Effects 0.000 claims description 27
- 125000005842 heteroatom Chemical group 0.000 claims description 27
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 27
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 25
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 25
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 24
- 229930192474 thiophene Natural products 0.000 claims description 24
- 150000003624 transition metals Chemical class 0.000 claims description 24
- 229910052723 transition metal Inorganic materials 0.000 claims description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 21
- 150000001491 aromatic compounds Chemical class 0.000 claims description 21
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 21
- 239000000377 silicon dioxide Substances 0.000 claims description 19
- 229910052752 metalloid Inorganic materials 0.000 claims description 17
- 150000002738 metalloids Chemical class 0.000 claims description 17
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 15
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 15
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 14
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
- 150000007942 carboxylates Chemical class 0.000 claims description 10
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 9
- 238000006467 substitution reaction Methods 0.000 claims description 9
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims description 8
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 claims description 8
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 8
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 8
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 8
- 125000005621 boronate group Chemical group 0.000 claims description 8
- 150000001721 carbon Chemical group 0.000 claims description 8
- 150000002240 furans Chemical class 0.000 claims description 8
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 8
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 8
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 8
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 239000002243 precursor Substances 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 7
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 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 claims description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 6
- 239000004305 biphenyl Chemical group 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 125000000707 boryl group Chemical group B* 0.000 claims description 6
- 229920001577 copolymer Polymers 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 6
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 6
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 5
- 239000004593 Epoxy Substances 0.000 claims description 5
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000003368 amide group Chemical group 0.000 claims description 5
- 125000006242 amine protecting group Chemical group 0.000 claims description 5
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 claims description 5
- 229910052732 germanium Inorganic materials 0.000 claims description 5
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims description 5
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 5
- 125000000061 phosphanyl group Chemical group [H]P([H])* 0.000 claims description 5
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 5
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 229910052718 tin Inorganic materials 0.000 claims description 5
- 125000003944 tolyl group Chemical group 0.000 claims description 5
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims description 4
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 4
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 4
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 claims description 4
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims description 4
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 229910002651 NO3 Inorganic materials 0.000 claims description 4
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000005163 aryl sulfanyl group Chemical group 0.000 claims description 4
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical group 0.000 claims description 4
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims description 4
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 claims description 4
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 4
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 4
- 239000004711 α-olefin Substances 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical compound C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
- 125000005577 anthracene group Chemical group 0.000 claims description 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
- 125000004467 aryl imino group Chemical class 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- 125000004997 halocarbonyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 150000003568 thioethers Chemical class 0.000 claims description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
- 150000003852 triazoles Chemical class 0.000 claims description 3
- 230000033444 hydroxylation Effects 0.000 claims description 2
- 238000005805 hydroxylation reaction Methods 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000005248 alkyl aryloxy group Chemical group 0.000 claims 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 2
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical class CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 claims 1
- HRYRBSWJGRISSR-UHFFFAOYSA-N [dicyano(isocyanato)-lambda4-sulfanyl] cyanate Chemical compound O=C=NS(C#N)(C#N)OC#N HRYRBSWJGRISSR-UHFFFAOYSA-N 0.000 claims 1
- 230000021523 carboxylation Effects 0.000 claims 1
- 238000006473 carboxylation reaction Methods 0.000 claims 1
- NONOKGVFTBWRLD-UHFFFAOYSA-N isocyanatosulfanylimino(oxo)methane Chemical compound O=C=NSN=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 claims 1
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 390
- 238000006243 chemical reaction Methods 0.000 description 203
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 190
- 239000000047 product Substances 0.000 description 168
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 154
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 130
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 125
- 238000000746 purification Methods 0.000 description 81
- 239000002585 base Substances 0.000 description 79
- 239000000741 silica gel Substances 0.000 description 78
- 229910002027 silica gel Inorganic materials 0.000 description 78
- 238000005481 NMR spectroscopy Methods 0.000 description 69
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 68
- 239000012230 colorless oil Substances 0.000 description 67
- 239000011780 sodium chloride Substances 0.000 description 65
- 239000010408 film Substances 0.000 description 64
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 62
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 61
- 238000005160 1H NMR spectroscopy Methods 0.000 description 58
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 49
- 150000001875 compounds Chemical class 0.000 description 43
- 150000001282 organosilanes Chemical class 0.000 description 37
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 34
- 235000019439 ethyl acetate Nutrition 0.000 description 34
- 125000004432 carbon atom Chemical group C* 0.000 description 29
- 239000001301 oxygen Substances 0.000 description 26
- 238000002474 experimental method Methods 0.000 description 25
- 239000011541 reaction mixture Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 239000000126 substance Substances 0.000 description 23
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 22
- 239000002904 solvent Substances 0.000 description 22
- 238000010828 elution Methods 0.000 description 21
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 125000003342 alkenyl group Chemical group 0.000 description 20
- 125000000524 functional group Chemical group 0.000 description 20
- 150000002390 heteroarenes Chemical class 0.000 description 19
- 239000000463 material Substances 0.000 description 19
- 239000007787 solid Substances 0.000 description 19
- 230000009257 reactivity Effects 0.000 description 18
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- BLRHMMGNCXNXJL-UHFFFAOYSA-N 1-methylindole Chemical compound C1=CC=C2N(C)C=CC2=C1 BLRHMMGNCXNXJL-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 15
- 150000004679 hydroxides Chemical class 0.000 description 15
- 239000007858 starting material Substances 0.000 description 15
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 15
- 150000004703 alkoxides Chemical class 0.000 description 14
- 230000007246 mechanism Effects 0.000 description 14
- 229910000077 silane Inorganic materials 0.000 description 14
- 230000009466 transformation Effects 0.000 description 14
- 238000010626 work up procedure Methods 0.000 description 14
- 238000004458 analytical method Methods 0.000 description 13
- 238000004587 chromatography analysis Methods 0.000 description 13
- 238000003776 cleavage reaction Methods 0.000 description 13
- UCXUKTLCVSGCNR-UHFFFAOYSA-N diethylsilane Chemical compound CC[SiH2]CC UCXUKTLCVSGCNR-UHFFFAOYSA-N 0.000 description 13
- 238000011065 in-situ storage Methods 0.000 description 13
- WYURNTSHIVDZCO-SVYQBANQSA-N oxolane-d8 Chemical compound [2H]C1([2H])OC([2H])([2H])C([2H])([2H])C1([2H])[2H] WYURNTSHIVDZCO-SVYQBANQSA-N 0.000 description 13
- 150000003623 transition metal compounds Chemical class 0.000 description 13
- YVBAUDVGOFCUSG-UHFFFAOYSA-N 2-pentylfuran Chemical compound CCCCCC1=CC=CO1 YVBAUDVGOFCUSG-UHFFFAOYSA-N 0.000 description 12
- 125000000304 alkynyl group Chemical group 0.000 description 12
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 12
- 230000003197 catalytic effect Effects 0.000 description 12
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- UZQBMULSJJJUHD-UHFFFAOYSA-N triethyl-[7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-benzothiophen-2-yl]silane Chemical compound C(C)[Si](C1=CC2=C(S1)C(=CC=C2)B1OC(C(O1)(C)C)(C)C)(CC)CC UZQBMULSJJJUHD-UHFFFAOYSA-N 0.000 description 1
- PVOUDDCZUTUILW-UHFFFAOYSA-N triethyl-[phenoxy(phenyl)methyl]silane Chemical compound C(C)[Si](C(C1=CC=CC=C1)OC1=CC=CC=C1)(CC)CC PVOUDDCZUTUILW-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
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- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
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Description
この出願は2014年8月6日付け出願の米国特許出願番号第62/033,975号;2014年12月19日付け出願の同第62/094,381号、および2015年4月2日付け出願の同第62/141,905号に対して優先権を主張し、それらの内容をすべての目的のためにここに参照することによって組み込む。
この発明は、ナショナル・サイエンス・ファウンデ-ション(連邦政府科学財団)によって与えられた認可番号第CHE1212767号の下で政府支援により行われた。政府は本発明において一定の権利をもつ。
本発明は、芳香族基質で、複素環式芳香族化合物の基質を含めたものを、水酸化物(特に水酸化カリウム)およびシラン試薬を用いてシリル化するための方法に指向する。
(R)4-mSi(H)m (I)
R-[-SiH(R)-O-]n-R (II)
式中、mは1、2、または3、好ましくは1または2であり;
(R)4-mSi(H)m (I)
R-[-SiH(R)-O-]n-R (II)
式中、mは1、2、または3(好ましくは1または2)であり、
nは10ないし100であり、および
各Rは、無関係に、随意に置換のC1-12アルキルまたはヘテロアルキル、随意に置換のC5-20アリ-ルまたはC4-20ヘテロアリ-ル、随意に置換のC6-30アルカリ-ルまたはC4-30ヘテロアルカリ-ル、随意に置換のC6-30アラルキルまたはヘテロアラルキル、随意に置換の-O-C1-12アルキルまたはヘテロアルキル、随意に置換の-O-C5-20アリ-ルまたは-O-C4-20ヘテロアリ-ル、随意に置換の-O-C6-30アルカリ-ルまたはC4-30ヘテロアルカリ-ル、または随意に置換の-O-C6-30アラルキルまたは-O-C4-30ヘテロアラルキル、および、置換される場合、置換基は、ホスホナト、ホスホリル、ホスファニル(phosphanyl)、ホスフィノ、スルホナト、C1-C20アルキルスルファニル、C5-C20アリ-ルスルファニル、C1-C20アルキルスルホニル、C5-C20アリ-ルスルホニル、C1-C20アルキルスルフィニル、C5-C20アリ-ルスルフィニル、スルホンアミド、アミノ、アミド、イミノ、ニトロ、ニトロソ、ヒドロキシ、C1-C20アルコキシ、C5-C20アリ-ルオキシ、C2-C20アルコキシカルボニル、C5-C20アリ-ルオキシカルボニル、カルボキシル、カルボキシラト、メルカプト、ホルミル、C1-C20チオエステル、シアノ、シアナト、チオシアナト、イソシアナト、チオイソシアナト、カルバモイル、エポキシ、スチレニル、シリル、シリルオキシ、シラニル、シロキサザニル、ボロナト、ボリル、またはハロゲン、または金属含有またはメタロイド(半金属)含有基でよく、そこでは、メタロイドはSnまたはGeであり、そこでは、置換基は、随意に、アルミナ、シリカ、または炭素が含まれる不溶性または難溶性の支持媒体にテザ-を提供することができる。
などのようなもので、たとえば、フェニレンオキシド、ナフタレンオキシド、またはアルキレンフェニレンオキシドのポリマ-またはコポリマ-などのようなものが含まれ、およびこれらの転換に影響を及ぼす方法は本開示の範囲内にあると考えられる。
式中、XはN-R’’、O、またはSであり、
YはH、N(R’’)2、O-R’’、またはS-R’’であり、
pは0ないし4、0ないし3、0ないし2、または0ないし1であり、
R’は、上記のように、官能基「Fn」であり、または(R’)pには、縮合脂環式、ヘテロ脂環式(例は、メチレン、エチレン、またはプロピレンリンク(結合)ジエ-テル)、アリ-ルまたはヘテロアリ-ル部分が含まれ、および
R’’は、アミン保護基または随意に置換されるアルキル、アリ-ル、ヘテロアリ-ル、アルカリ-ルまたはアルカヘテロアリ-ル、好ましくは随意に置換されるC1-C6アルキル、フェニル、トリル、ベンジル、またはフェネチルである。
式中、X、Y、R'、R''およびpは上記に規定するようなものである。なお、いずれの場合も、表示
は、いずれかの芳香環上の置換を可能にすることが意図されることに注目される。
(R)4-mSi(H)m (I)
R-[-SiH(R)-O-]n-R (II)
式中、mは1、2、または3であり、
nは10ないし100であり、および
各Rは、無関係に、随意に置換のC1-12アルキルまたはヘテロアルキル、随意に置換のC5-20アリ-ルまたはC4-20ヘテロアリ-ル、随意に置換のC6-30アルカリ-ルまたはヘテロアルカリ-ル、随意に置換のC5-30アラルキルまたはヘテロアラルキル、随意に置換の-O-C1-12アルキルまたはヘテロアルキル、随意に置換の-O-C5-20アリ-ルまたは-O-C4-20ヘテロアリ-ル、随意に置換の-O-C5-30アルカリ-ルまたはヘテロアルカリ-ル、または随意に置換の-O-C5-30アラルキルまたはヘテロアラルキル、および、置換される場合、置換基は、ホスホナト、ホスホリル、ホスファニル、ホスフィノ、スルホナト、C1-C20アルキルスルファニル、C5-C20アリ-ルスルファニル、C1-C20アルキルスルホニル、C5-C20アリ-ルスルホニル、C1-C20アルキルスルフィニル、C5-C20アリ-ルスルフィニル、スルホンアミド、アミノ、アミド、イミノ、ニトロ、ニトロソ、ヒドロキシ、C1-C20アルコキシ、C5-C20アリ-ルオキシ、C2-C20アルコキシカルボニル、C5-C20アリ-ルオキシカルボニル、カルボキシル、カルボキシラト、メルカプト、ホルミル、C1-C20チオエステル、シアノ、シアナト、チオシアナト、イソシアナト、チオイソシアナト、カルバモイル、エポキシ、スチレニル、シリル、シリルオキシ、シラニル、シロキサザニル、ボロナト、ボリル、またはハロゲン、または金属含有またはメタロイド(半金属)含有基でよく、そこでは、メタロイドはSnまたはGeであり、そこでは、置換基は、随意に、アルミナ、シリカ、または炭素が含まれる不溶性または難溶性の支持媒体にテザ-を提供することができる。
式中、XはN-R’’、O、またはSであり、
YはH、N(R’’)2、O-R’’、またはS-R’’であり、
pは0ないし4、0ないし3、0ないし2、または0ないし1であり、
R’は、上記のように、官能基「Fn」であり、または(R’)pには、随意に置換される縮合脂環式、ヘテロ脂環式(例は、メチレン、エチレン、またはプロピレン結合ジエ-テル)、アリ-ルまたはヘテロアリ-ル部分が含まれ、および
R’’は、アミン保護基または随意に置換されるアルキル、アリ-ル、ヘテロアリ-ル、アルカリ-ルまたはアルカヘテロアリ-ル、好ましくは随意に置換されるC1-C6アルキル、フェニル、トリル、ベンジル、またはフェネチルである。
式中、X、Y、R'、R''およびpは上記に規定するようなものである。各場合において、表示
は、いずれかの芳香環上の置換を可能にすることが意図される。
(R)4-mSi(H)m (I)
R-[-SiH(R)-O-]n-R (II)
式中、mは1、2、または3(好ましくは1または2)であり、
nは10ないし100であり、および
および各Rは、無関係に、随意に置換のC1-12アルキルまたはヘテロアルキル、随意に置換のC5-20アリ-ルまたはC4-20ヘテロアリ-ル、随意に置換のC6-30アルカリ-ルまたはヘテロアルカリ-ル、随意に置換のC6-30アラルキルまたはヘテロアラルキル、随意に置換の-O-C1-12アルキルまたはヘテロアルキル、随意に置換の-O-C5-20アリ-ルまたはC4-20ヘテロアリ-ル、随意に置換の-O-C6-30アルカリ-ルまたは-O-C4-30ヘテロアルカリ-ル、または随意に置換の-O-C6-30アラルキルまたは-O-C4-30ヘテロアラルキル、および、置換される場合、置換基は、ホスホナト、ホスホリル、ホスファニル(phosphanyl)、ホスフィノ、スルホナト、C1-C20アルキルスルファニル、C5-C20アリ-ルスルファニル、C1-C20アルキルスルホニル、C5-C20アリ-ルスルホニル、C1-C20アルキルスルフィニル、C5-C20アリ-ルスルフィニル、スルホンアミド、アミノ、アミド、イミノ、ニトロ、ニトロソ、ヒドロキシ、C1-C20アルコキシ、C5-C20アリ-ルオキシ、C2-C20アルコキシカルボニル、C5-C20アリ-ルオキシカルボニル、カルボキシル、カルボキシラト、メルカプト、ホルミル、C1-C20チオエステル、シアノ、シアナト、チオシアナト、イソシアナト、チオイソシアナト、カルバモイル、エポキシ、スチレニル、シリル、シリルオキシ、シラニル、シロキサザニル、ボロナト、ボリル、またはハロゲン、または金属含有またはメタロイド(半金属)含有基でよく、そこでは、メタロイドはSnまたはGeであり、そこでは、置換基は、随意に、アルミナ、シリカ、または炭素が含まれる不溶性または難溶性の支持媒体にテザ-を提供することができる。
式中、XはN-R’’、O、またはSであり、
YはH、N(R’’)2、O-R’’、またはS-R’’であり、
pは0ないし4、0ないし3、0ないし2、または0ないし1であり、
R’は、上記のように、官能基「Fn」であり、または(R’)pは、随意に置換される縮合脂環式、ヘテロ脂環式、アリ-ルまたはヘテロアリ-ル部分であり、および
R’’は、アミン保護基または随意に置換されるアルキル、アリ-ル、ヘテロアリ-ル、アルカリ-ルまたはアルカヘテロアリ-ル、好ましくは随意に置換されるC1-C6アルキル、フェニル、トリル、ベンジル、またはフェネチルである。
式中、X、Y、R'、R''およびpは上記に規定するようなものである。各場合において、表示
は、いずれかの芳香環上の置換を可能にすることが意図される。
より一層低い温度では、この反応は生成物の混合物を提供すると考えられ、単一の生成物を同定することはできなかった。環外アミンに対してオルトをシリル化するための見かけの通常の傾向は、二つのメチル基に関係がある立体的なバルクによって抑制されることは、確認されていないが、可能である。
本反応は、基本手順に従い、1-メトキシナフタレン(79mg、0.5ミリモル、1当量)、KOt-Bu(11.2mg、0.1ミリモル、0.1当量)およびEt3SiH(240マイクロリットル、1.5ミリモル、3当量)を1mLのテトラヒドロフランにおいて65℃で65時間加熱することによって行った。反応物をジエチルエ-テル(1mL)で希釈し、水(0.5mL)でクエンチし、および有機相をGC-MS、GC-FIDおよび1H NMR分析によって分析した。GC-MSおよびGC-FID(トリデカン標準)による分析は、アリ-ルC-O開裂生成物ナフタレンおよびアルキルC-O結合開裂生成物ナフト-ルの生成をそれぞれ13%および8%の収率で、特にシリル化種を完全に除外することを明らかにした。
本反応は、基本手順に従い、フェニルエ-テル(85mg、0.5mmol、1当量)、KOt-Bu(11mg、0.10mmol、0.2当量)およびEt2SiH2(194μl、1.5mmol、3当量)を、テトラヒドロフラン1mLにおいて65℃で65時間加熱することによって行った。水性ワ-クアップの後、粗反応混合物を、ヘキサン:トリエチルアミンの80:2混合物を用いるシリカでのクロマトグラフィ-によって精製して、68mg(20%)の表題化合物を無色油状固体として取得した。1H NMR(500MHz、THF-d8)δ7.64-7.57(m、2H)、7.55(dd、J=7.3、1.8Hz、1H)、7.41(ddd、J=8.3、7.2、1.8Hz、1H)、7.15(dd、J=8.3、1.0Hz、1H)、7.14-7.09(m、2H)、4.34(Si-H)(p-様、J=1.2Hz、1H)、1.06-0.95(m、12H)、0.92-0.82(m、8H)。13C NMR(126MHz、THF-d8)δ166.04、161.43、139.74、137.00、135.55、135.05、132.12、130.19、128.79、123.56、123.37、118.41、9.06、7.93、6.70、4.83。HRMS:[C20H27OSi2]計算値339.1601、測定値339.1607。
本反応は、基本手順に従い、KOt-Bu(11.2mg、0.1mmol、20mol%)、オキシジベンゼン(85.0mg、0.5mmol)、およびEt3SiH(240μL、1.5mmol、3当量)を溶媒なしで85℃にて120時間加熱することによって行った。望ましい生成物17b(84.5mg、収率55%)は、シリカゲルフラッシュクロマトグラフィ-(100%ヘキサン)による精製後に無色油状物として取得された。Rf=0.4(100%ヘキサン)。1H NMR(500MHz、CDCl3)δ7.52-7.46(m、1H)、7.38-7.25(m、3H)、7.10(t、J=7.4Hz、2H)、7.00(d、J=7.9Hz、2H)、6.81(d、J=8.1Hz、1H)、0.97(t、J=7.9Hz、9H)、0.85(q、J=7.9Hz、6H)。
13C NMR(126MHz、CDCl3)δ144.01、141.12、140.18、137.29、134.13、132.41、129.70、128.09、124.45、124.18、123.69、122.33、-1.42。HRMS:[C16H16SSi]算出268.0743、測定268.0742
この傾向は、置換チオフェン3mおよびフラン3nとの間の競争において裏付けられた。競争実験の手順は次のとおりである。
1.Zhang(チャン), F.、Wu(ウ-), D.、Xu(ス-), Y.およびFeng(フォン), X.、Thiophene-based conjugated oligomers for organic solar cells.(有機太陽電池のためのチオフェンベ-ス共役オリゴマ-)、J. Mater. Chem.(ジャ-ナル・オブ・マテリアルズ・ケミストリ-)、21、17590-17600(2011)。
2.Showell(ショウエル), G. A.およびMills(ミルズ), J. S.、Chemistry challenges in lead optimization: silicon isosteres in drug discovery.(リ-ド最適化の化学的課題:創薬におけるシリコンアイソスタ-)Drug Discov. Today(ドラッグ・ディスカバリ-・トゥデイ)8, 551-556(2003)。
3.Franz(フランツ), A. K.およびWilson(ウィルソン), S. O.、Organosilicon molecules with medicinal applications.(医薬用途の有機シリコン分子)、J. Med. Chem.(ジャ-ナル・オブ・メディシナル・ケミストリ-)、56, 388-405(2013)。
4.Ball(ボ-ル), L. T., Lloyd-Jones(ロイド・ジョ-ンズ), G. C.およびRussell(ラッセル), C. A.、Gold-catalyzed direct arylation.(金触媒直接アリ-ル化)、Science(サイエンス)、337, 1644-1648(2012)。
5.Denmark(デンマ-ク), S. E.およびBaird(ベア-ド), J. D.、Palladium-catalyzed cross-coupling reactions of silanolates: a paradigm shift in silicon-based cross-coupling reactions.(シラノレ-トのパラジウム触媒クロスカップリング反応:ケイ素ベ-スクロスカップリング反応でのパラダイムシフト)、Chem. Eur. J.(ケミストリ-・ア・ヨ-ロピアン・ジャ-ナル)、12, 4954-4963(2006)。
6.Langkopf(ランコフ), E.およびSchinzer(シンザ-), D.、Uses of silicon-containing compounds in the synthesis of natural products.(自然生成物の合成におけるケイ素含有化合物の使用)、Chem. Rev.(ケミカル・リビュ-)、95, 1375-1408(1995)。
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Claims (27)
- 芳香族有機基質をシリル化するための方法であって、
該方法は、芳香族環部分が含まれる有機基質を、(a)少なくとも一のヒドロシランおよび(b)水酸化カリウム(KOH)が含まれる混合物と、基質をシリル化するのに十分な条件下に接触させることを含み、該基質をシリル化するのに十分な条件は、40℃~165℃の範囲の温度で、(a)少なくとも一のヒドロシランおよび(b)水酸化カリウム(KOH)の混合物と共に基質を加熱することを含み、
該方法は、シリル化された有機基質の形成をもたらし、
該シリル化された有機基質が、以前に炭素-水素結合を有していた位置に対応する位置に、炭素-ケイ素結合を有する、方法。 - 前記有機基質中の前記炭素-水素結合が、炭素-水素結合を有する前記芳香族部分上の位置に対応し、但し、以下の場合、即ち:
(a)前記シリル化された有機基質が、炭素環式アリール部分に対してアルファのアルキル置換基の炭素に炭素-ケイ素結合を有する場合において、前記有機基質が、アルキル置換基を有する炭素環式アリール部分を含む炭化水素である場合、
(b)前記シリル化された有機基質が、チオエーテルの硫黄に対してアルファの炭素に炭素-ケイ素結合を有する場合において、前記芳香族部分が、前記芳香族環部分の環の炭素原子に結合したアルキルチオエーテル置換基を有するものである場合、
(c)前記シリル化された有機基質が、ヘテロアリール環に対してアルファのアルキル置換の炭素に炭素-ケイ素結合を有する場合において、前記芳香族部分が、環内へテロ原子を含むヘテロアリール環であって、該ヘテロアリール環が、環内へテロ原子に隣接する位置に、少なくとも1つのアルキル置換基を有し且つC-H置換基を有しない場合、
を除く、請求項1に記載の方法。 - 混合物および基質は、故意に添加された遷移金属触媒を含まない、請求項1の方法。
- 少なくとも一のヒドロシランには、式(I)または式(II)のヒドロシランが含まれる、請求項1、2又は3の方法:
(R)4-mSi(H)m・・・(I) R-[-SiH(R)-O-]n-R・・・(II)
式中、mは1、2、または3、
nは10ないし100であり、および
各Rは、無関係に、随意に置換されるC1-12アルキルまたはヘテロアルキル、随意に置換されるC5-20アリールまたはC4-20ヘテロアリール、随意に置換されるC6-30アルカリールまたはC4-30ヘテロアルカリール、随意に置換されるC6-30アラルキルまたはC4-30ヘテロアラルキル、随意に置換される-O-C1-12アルキルまたはヘテロアルキル、随意に置換される-O-C5-20アリールまたは-O-C4-20ヘテロアリール、随意に置換される-O-C6-30アルカリールまたはヘテロアルカリール、または随意に置換される-O-C6-30アラルキルまたは-O-C4-30ヘテロアラルキル、および、置換される場合、置換基はホスホナト、ホスホリル、ホスファニル、ホスフィノ、スルホナト、C1-C20アルキルスルファニル、C5-C20アリールスルファニル、C1-C20アルキルスルホニル、C5-C20アリールスルホニル、C1-C20アルキルスルフィニル、C5-C20アリールスルフィニル、スルホンアミド、アミノ、アミド、イミノ、ニトロ、ニトロソ、ヒドロキシル、C1-C20アルコキシ、C5-C20アリールオキシ、C2-C20アルコキシカルボニル、C5-C20アリールオキシカルボニル、カルボキシル、カルボキシラト、メルカプト、フォルミル、C1-C20チオエステル、シアノ、シアナト、チオシアナト、イソシアナート、チオイソシアナート、カルバモイル、エポキシ、スチレニル、シリル、シリルオキシ、シラニル、シロキサザニル、ボロナト、ボリル、またはハロゲン、または金属含有もしくはメタロイド含有基であることができ、そこでは、メタロイドはSnまたはGeであり、そこでは、置換基は随意に不溶性または難溶性のアルミナ、シリカ、または炭素が含まれる支持媒体にテザーを提供することができる。 - ヒドロシランは(R)3SiHであり、各Rは無関係にC1-6アルキルである、請求項4の方法。
- 前記芳香族部分には、メチル置換基を有する、ベンゼン、ビフェニル、ナフタレン、またはアントラセン環構造が含まれ、
前記シリル化された有機基質は、該メチル置換基上に炭素-ケイ素結合を有する、請求項1、2又は3の方法。 - 芳香族部分には、環外メチルチオエーテルが含まれ、
前記シリル化された有機基質は、該チオエーテルのメチル置換基上に炭素-ケイ素結合を有する、請求項1、2又は3の方法。 - 有機基質には、ヘテロアリール部分が含まれる、請求項1、2又は3の方法。
- 基質には、随意に置換されるフラン、ピロール、チオフェン、ピラゾール、イミダゾール、ベンゾフラン、ベンゾピロール、ベンゾチオフェン、インドール、アザインドール、ジベンゾフラン、キサンテン、ジベンゾピロール、またはジベンゾチオフェンが含まれる、請求項8の方法。
- 有機芳香族基質には、以下の部分の少なくとも一が含まれる、請求項1、2又は3の方法:
Yは、H、N(R'')2、O-R''、またはS-R''であり、
pは0ないし4であり、
R'は、C1-24アルキル、ハロ、スルフヒドリル、アルコキシ、アリールオキシ、アラルキルオキシ、アルカリールオキシ、アシル、アシルオキシ、アルコキシカルボニル、アリールオキシカルボニル、ハロカルボニル、アルキルカルボナト、アリールカルボナト、カルボキシラト(-COO-)、ジアルキル置換カルバモイル、ジハロアルキル置換カルバモイル、ジアリール置換カルバモイル、ジアルキル置換チオカルバモイル、ジアリール置換チオカルバモイル、ジ-N-アルキル置換チオカルバモイル、シアノ、シアナト、チオシアナト、ジアルキル置換アミノ、ジアリール置換アミノ、アリールイミノ〔-CR=N(アリール)、ここで、R=アルキル、アリール、アルカリール、アラルキル〕、ニトロ、ニトロソ、アルキルスルファニル、アリールスルファニル、アルキルスルフィニル、アリールスルフィニル、アルキルスルホニル、ボロナト〔-B(OR)2、ここで、Rはアルキルまたは他のヒドロカルビルである。〕、または(R')pには、随意に置換される縮合メチレンリンクジエーテル、エチレンリンクジエーテル、またはプロピレンリンクジエーテル、アリールまたはヘテロアリール部分が含まれ、および
R''は、アミン保護基または随意に置換されるアルキル、アリール、ヘテロアリール、アルカリールまたはアルカヘテロアリールである。 - 基質には、次の部分の少なくとも一が含まれる、請求項1、2又は3の方法:
pは0ないし4であり、
R'は、C1-24アルキル、ハロ、スルフヒドリル、アルコキシ、アリールオキシ、アラルキルオキシ、アルカリールオキシ、アシル、アシルオキシ、アルコキシカルボニル、アリールオキシカルボニル、ハロカルボニル、アルキルカルボナト、アリールカルボナト、カルボキシラト(-COO-)、ジアルキル置換カルバモイル、ジハロアルキル置換カルバモイル、ジアリール置換カルバモイル、ジアルキル置換チオカルバモイル、ジアリール置換チオカルバモイル、ジ-N-アルキル置換チオカルバモイル、シアノ、シアナト、チオシアナト、ジアルキル置換アミノ、ジアリール置換アミノ、アリールイミノ〔-CR=N(アリール)、ここで、R=アルキル、アリール、アルカリール、アラルキル〕、ニトロ、ニトロソ、アルキルスルファニル、アリールスルファニル、アルキルスルフィニル、アリールスルフィニル、アルキルスルホニル、ボロナト〔-B(OR)2、ここで、Rはアルキルまたは他のヒドロカルビルである。〕、または(R')pには、随意に置換される縮合メチレンリンクジエーテル、エチレンリンクジエーテル、またはプロピレンリンクジエーテル、アリールまたはヘテロアリール部分が含まれ、および
R''は、アミン保護基または随意に置換されるアルキル、アリール、ヘテロアリール、アルカリールまたはアルカヘテロアリールである。 - 芳香族部分を含む有機基質は、ポリマー、オリゴマー、またはポリマーの前駆体である、請求項1、2又は3の方法。
- 前記シリル化された有機基質は、シリル化生成物が、ビアロマティック生成物を形成するために第二芳香族化合物と接合されるのに十分な条件下、さらに反応させられる、請求項1、2又は3の方法。
- 前記シリル化された有機基質は、シリル化された有機基質を、ヒドロキシル化(保護または遊離ヒドロキシル)、アルコキシル化(またはアリールオキシル化)、またはアルキルもしくはアリールカルボキシル化生成物に変換させるのに十分な条件下、さらに反応させられる、請求項1、2又は3の方法。
- 前記シリル化された有機基質は、シリル化された有機基質を、芳香族アルファオレフィン生成物に変換させるのに十分な条件下、さらに反応させられる、請求項1、2又は3の方法。
- 前記シリル化された有機基質は、シリル化された有機基質を、芳香族ハライド、ナイトラートまたはナイトライトに変換させるのに十分な条件下、さらに反応させられる、請求項1、2又は3の方法。
- 前記シリル化された有機基質は、シリル化された有機基質を、芳香族ボロン酸ハライドまたはボロン酸エステルに変換させるのに十分な条件下、さらに反応させられる、請求項1、2又は3の方法。
- 前記シリル化された有機基質は、シリル化チオフェン生成物であり、該シリル化チオフェン生成物は、シリル化チオフェン生成物を、交互チオフェン-ペルフルオロアレーンコポリマーに変換させるのに十分な条件下、さらに反応させられる、請求項1、2又は3の方法。
- 前記有機基質には、フラン、ピロール、チオフェン、ピラゾール、イミダゾール、トリアゾール、イソキサゾール、オキサゾール、チアゾール、イソチアゾール、オキサジアゾール、ピリジン、ピリダジン、ピリミジン、ピラジン、トリアゾン、ベンゾフラン、ベンゾチオフェン、イソベンゾフラン、イソベンゾチオフェン、インドール、イソインドール、インドリジン、インダゾール、アザインドール、ベンズイソオキサゾール、ベンズオキサゾール、キノリン、イソキノリン、シンノリン、キナゾリン、ナフチリジン、2,3-ジヒドロベンゾフラン、2,3-ジヒドロベンゾピロール、2,3-ジヒドロベンゾチオフェン、ジベンゾフラン、キサンテン、ジベンゾピロール、又はジベンゾチオフェン部分が含まれる、請求項8の方法。
- mが1又は2である、請求項4の方法。
- 各Rが、無関係に、C1-C6アルキル、フェニル、トリル、ベンジル、フェネチル、又はピリジニルである、請求項4の方法。
- 各R''が、無関係に、C1-C6アルキル、フェニル、トリル、ベンジル、又はフェネチルである、請求項10の方法。
- 前記ヒドロシランが、(R)2Si(H)2である、請求項4の方法。
- Rが、無関係に:
(a)随意に置換される環状アルキル、随意に置換される分岐状アルキル、随意に置換される環状ヘテロアルキル、若しくは随意に置換される分岐状ヘテロアルキル、又は
(b)随意に置換されるC1-12アルキル、随意に置換されるヘテロアリール、若しくは随意に置換されるC2-12ヘテロシクロアルキル、又は
(c)tert-ブチル、シアノ置換イソプロピル、ピリジニル、若しくはアルキル置換ヘテロシクロアルキル
である、請求項25の方法。 - 有機基質には、ヘテロアリール部分が含まれる、請求項25又は26の方法。
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