JP2014532736A - アリールアミンの調製方法 - Google Patents
アリールアミンの調製方法 Download PDFInfo
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- JP2014532736A JP2014532736A JP2014540341A JP2014540341A JP2014532736A JP 2014532736 A JP2014532736 A JP 2014532736A JP 2014540341 A JP2014540341 A JP 2014540341A JP 2014540341 A JP2014540341 A JP 2014540341A JP 2014532736 A JP2014532736 A JP 2014532736A
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- 238000000034 method Methods 0.000 title claims description 55
- 238000002360 preparation method Methods 0.000 title claims description 5
- 150000004982 aromatic amines Chemical class 0.000 title 1
- -1 amino compound Chemical class 0.000 claims abstract description 65
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 125000001769 aryl amino group Chemical group 0.000 claims abstract description 13
- 238000005859 coupling reaction Methods 0.000 claims abstract description 13
- 125000003118 aryl group Chemical group 0.000 claims description 89
- 150000003254 radicals Chemical class 0.000 claims description 41
- 239000002585 base Substances 0.000 claims description 39
- 239000003054 catalyst Substances 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical class CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 229910052723 transition metal Inorganic materials 0.000 claims description 11
- 150000003624 transition metals Chemical class 0.000 claims description 11
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 9
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 8
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 8
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 claims description 8
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 claims description 4
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 claims description 4
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 claims description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 4
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 claims description 4
- 125000004001 thioalkyl group Chemical group 0.000 claims description 4
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 4
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 claims description 3
- 229960005544 indolocarbazole Drugs 0.000 claims description 3
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 150000002902 organometallic compounds Chemical class 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- 238000007832 transition metal-catalyzed coupling reaction Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 33
- 239000003446 ligand Substances 0.000 description 17
- 239000000047 product Substances 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 239000007858 starting material Substances 0.000 description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000006227 byproduct Substances 0.000 description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
- 0 *c1cc(Nc2c(*)cccc2*)c(*)cc1 Chemical compound *c1cc(Nc2c(*)cccc2*)c(*)cc1 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 3
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- CETVQRFGPOGIQJ-UHFFFAOYSA-N lithium;hexane Chemical compound [Li+].CCCCC[CH2-] CETVQRFGPOGIQJ-UHFFFAOYSA-N 0.000 description 3
- MAINCNYZMOMWRA-UHFFFAOYSA-N n-(2,4-dimethylphenyl)-2,4-dimethylaniline Chemical compound CC1=CC(C)=CC=C1NC1=CC=C(C)C=C1C MAINCNYZMOMWRA-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000003003 phosphines Chemical class 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- OVFJHQBWUUTRFT-UHFFFAOYSA-N 1,2,3,4-tetrahydrotetrazine Chemical compound C1=CNNNN1 OVFJHQBWUUTRFT-UHFFFAOYSA-N 0.000 description 2
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 2
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 2
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 2
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 2
- UUSUFQUCLACDTA-UHFFFAOYSA-N 1,2-dihydropyrene Chemical compound C1=CC=C2C=CC3=CCCC4=CC=C1C2=C43 UUSUFQUCLACDTA-UHFFFAOYSA-N 0.000 description 2
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 2
- USYCQABRSUEURP-UHFFFAOYSA-N 1h-benzo[f]benzimidazole Chemical compound C1=CC=C2C=C(NC=N3)C3=CC2=C1 USYCQABRSUEURP-UHFFFAOYSA-N 0.000 description 2
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 2
- LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical compound C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 description 2
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 2
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 2
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 2
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
- 238000007125 Buchwald synthesis reaction Methods 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 101150003085 Pdcl gene Proteins 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 2
- WMUIZUWOEIQJEH-UHFFFAOYSA-N benzo[e][1,3]benzoxazole Chemical compound C1=CC=C2C(N=CO3)=C3C=CC2=C1 WMUIZUWOEIQJEH-UHFFFAOYSA-N 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010537 deprotonation reaction Methods 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
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- 239000012429 reaction media Substances 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- FICPQAZLPKLOLH-UHFFFAOYSA-N tricyclohexyl phosphite Chemical compound C1CCCCC1OP(OC1CCCCC1)OC1CCCCC1 FICPQAZLPKLOLH-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- SJHCUXCOGGKFAI-UHFFFAOYSA-N tripropan-2-yl phosphite Chemical compound CC(C)OP(OC(C)C)OC(C)C SJHCUXCOGGKFAI-UHFFFAOYSA-N 0.000 description 1
- QOPBTFMUVTXWFF-UHFFFAOYSA-N tripropyl phosphite Chemical compound CCCOP(OCCC)OCCC QOPBTFMUVTXWFF-UHFFFAOYSA-N 0.000 description 1
- KCTAHLRCZMOTKM-UHFFFAOYSA-N tripropylphosphane Chemical compound CCCP(CCC)CCC KCTAHLRCZMOTKM-UHFFFAOYSA-N 0.000 description 1
- YGPLLMPPZRUGTJ-UHFFFAOYSA-N truxene Chemical compound C1C2=CC=CC=C2C(C2=C3C4=CC=CC=C4C2)=C1C1=C3CC2=CC=CC=C21 YGPLLMPPZRUGTJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/10—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/54—Ortho- or ortho- and peri-condensed systems containing more than five condensed rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
Arは、5ないし60個の芳香族環原子を有する芳香族環系であり、1つ以上のラジカルR1により置換されていてもよく、
Eは、出現する毎に、同一にまたは異なって、単結合、C(R1)2、C=O、Si(R1)2、NR1、OおよびSから選択され、
Rは、出現する毎に、同一にまたは異なって、H、1ないし20個のC原子を有する直鎖アルキル基、または3ないし20個のC原子を有する分枝もしくは環状アルキル基、または2ないし20個のC原子を有するアルケニルもしくはアルキニル基(ここで、上述した基は各々1つ以上のラジカルR1により置換されていてもよく、上述した基の1つ以上のCH2基は−R1C=CR1−、−C≡C−、Si(R1)2、C=O、C=S、C=NR1、−C(=O)O−、−C(=O)NR1−、NR1、P(=O)(R1)、−O−、−S−、SOまたはSO2により置きかえられていてもよく、上述した基の1つ以上のH原子はD、F、Cl、Br、I、CNまたはNO2により置きかえられていてもよい)、または5ないし60個の芳香族環原子を有する芳香族環系(各々の場合に1つ以上のラジカルR1により置換されていてもよい)から選択され、ここでラジカルRは互いに連結されていてもよく、環を形成していてもよく、窒素原子上の1つ以下の基RはHと等しく、
R1は、同一にまたは異なって、出現する毎に、H、D、F、Cl、Br、I、B(OR2)2、CHO、C(=O)R2、CR2=C(R2)2、CN、C(=O)OR2、C(=O)N(R2)2、Si(R2)3、N(R2)2、NO2、P(=O)(R2)2、OSO2R2、OR2、S(=O)R2、S(=O)2R2、1ないし20個のC原子を有する、直鎖アルキル、アルコキシもしくはチオアルキル基、または3ないし20個のC原子を有する、分枝もしくは環状アルキル、アルコキシもしくはチオアルキル基、または2ないし20個のC原子を有するアルケニルもしくはアルキニル基(ここで、上述した基は各々1つ以上のラジカルR2により置換されていてもよく、上述した基の1つ以上のCH2基は−R2C=CR2−、−C≡C−、Si(R2)2、C=O、C=S、C=NR2、−C(=O)O−、−C(=O)NR2−、NR2、P(=O)(R2)、−O−、−S−、SOまたはSO2により置きかえられていてもよく、上述した基の1つ以上のH原子は、D、F、Cl、Br、I、CNまたはNO2により置きかえられていてもよい)、または5ないし30個の芳香族環原子を有する芳香族環系(各々の場合に、1つ以上のラジカルR2により置換されていてもよい)、または5ないし30個の芳香族環原子を有するアリールオキシ基(1つ以上のラジカルR2により置換されていてもよい)から選択され、ここで2つ以上のラジカルR1は互いに連結されていてもよく、環を形成していてもよく、
R2は、出現する毎に、同一にまたは異なって、H、D、Fまたは1ないし20個のC原子を有する脂肪族、芳香族もしくはヘテロ芳香族有機ラジカル(さらに、1つ以上のH原子はDまたはFにより置きかえられていてもよい)であり、ここで2つ以上の置換基R2は互いに連結されていてもよく、環を形成していてもよく、
Xは、出現する毎に、同一にまたは異なって、任意の所望の脱離基であり、
kは、出現する毎に、同一にまたは異なって、0または1であり、ここでk=ゼロならば、基Eは存在せず、
nは1ないし10の値を有し、
ここで、下記式の化合物
Zは、基XもYも結合していなければ、出現する毎に、同一にまたは異なって、CR1またはNであり、基XまたはYが結合していれば、Cと等しく、
Yは、出現する毎に、同一にまたは異なって、B(R1)、C(R1)2、Si(R1)2、C=O、C=NR1、C=C(R1)2、O、S、S=O、SO2、N(R1)、P(R1)およびP(=O)R1から選択され、
R1は、上で示したように定義され、
a、b、cおよびdは、出現する毎に、同一にまたは異なって、0または1であり、ここで、aとbの合計はゼロより大きく、cとdの合計はゼロより大きい。
Claims (15)
- 少なくとも1つのアリールアミノ基を含む化合物の調製方法であって、アミノ化合物とアリール化合物との間の、少なくとも1種の遷移金属で触媒されるカップリング反応を含み、少なくとも33の、ジメチルスルホキシドに基づくpKa値を有する塩基を使用することを特徴とする方法。
- 請求項1に記載の方法であって、前記塩基は前記アミノ化合物のpKa値より少なくとも数値が6大きいpKa値を有することを特徴とする方法。
- 請求項1または2に記載の方法であって、前記塩基は、少なくとも34、特に好ましくは少なくとも36の、ジメチルスルホキシドに基づくpKa値を有することを特徴とする方法。
- 請求項1ないし3のいずれか1項に記載の方法であって、前記塩基は、アルカリ金属またはアルカリ土類金属の対イオンをもつアミドおよびアルカリ金属またはアルカリ土類金属の対イオンをもつ形式的に負に荷電した炭素原子を含む有機金属化合物から選択されることを特徴とする方法。
- 請求項1ないし4のいずれか1項に記載の方法であって、前記アミノ化合物はジアリールアミノ化合物であることを特徴とする方法。
- 請求項1ないし5のいずれか1項に記載の方法であって、触媒が存在し、前記触媒は周期表の7、8、9、10および11族から選択される少なくとも1種の遷移金属を含む化合物であることを特徴とする方法。
- 請求項1ないし6のいずれか1項に記載の方法であって、触媒が存在し、前記触媒は鉄、ニッケル、銅、パラジウムおよび白金から選択される少なくとも1種の金属を含む化合物であることを特徴とする方法。
- 請求項1ないし7のいずれか1項に記載の方法であって、以下のスキームに対応し、
Arは、5ないし60個の芳香族環原子を有する芳香族環系であり、1つ以上のラジカルR1により置換されていてもよく、
Eは、出現する毎に、同一にまたは異なって、単結合、C(R1)2、C=O、Si(R1)2、NR1、OおよびSから選択され、
Rは、出現する毎に、同一にまたは異なって、H、1ないし20個のC原子を有する直鎖アルキル基、または3ないし20個のC原子を有する分枝もしくは環状アルキル基、または2ないし20個のC原子を有するアルケニルもしくはアルキニル基(ここで、上述した基は各々1つ以上のラジカルR1により置換されていてもよく、上述した基の1つ以上のCH2基は−R1C=CR1−、−C≡C−、Si(R1)2、C=O、C=S、C=NR1、−C(=O)O−、−C(=O)NR1−、NR1、P(=O)(R1)、−O−、−S−、SOまたはSO2により置きかえられていてもよく、上述した基の1つ以上のH原子はD、F、Cl、Br、I、CNまたはNO2により置きかえられていてもよい)、または5ないし60個の芳香族環原子を有する芳香族環系(各々の場合に1つ以上のラジカルR1により置換されていてもよい)から選択され、ここでラジカルRは互いに連結されていてもよく、環を形成していてもよく、窒素原子上の1つ以下の基RはHと等しく、
R1は、同一にまたは異なって、出現する毎に、H、D、F、Cl、Br、I、B(OR2)2、CHO、C(=O)R2、CR2=C(R2)2、CN、C(=O)OR2、C(=O)N(R2)2、Si(R2)3、N(R2)2、NO2、P(=O)(R2)2、OSO2R2、OR2、S(=O)R2、S(=O)2R2、1ないし20個のC原子を有する、直鎖アルキル、アルコキシもしくはチオアルキル基、または3ないし20個のC原子を有する、分枝もしくは環状アルキル、アルコキシもしくはチオアルキル基、または2ないし20個のC原子を有するアルケニルもしくはアルキニル基(ここで、上述した基は各々1つ以上のラジカルR2により置換されていてもよく、上述した基の1つ以上のCH2基は−R2C=CR2−、−C≡C−、Si(R2)2、C=O、C=S、C=NR2、−C(=O)O−、−C(=O)NR2−、NR2、P(=O)(R2)、−O−、−S−、SOまたはSO2により置きかえられていてもよく、上述した基の1つ以上のH原子は、D、F、Cl、Br、I、CNまたはNO2により置きかえられていてもよい)、または5ないし30個の芳香族環原子を有する芳香族環系(各々の場合に、1つ以上のラジカルR2により置換されていてもよい)、または5ないし30個の芳香族環原子を有するアリールオキシ基(1つ以上のラジカルR2により置換されていてもよい)から選択され、ここで2つ以上のラジカルR1は互いに連結されていてもよく、環を形成していてもよく、
R2は、出現する毎に、同一にまたは異なって、H、D、Fまたは1ないし20個のC原子を有する脂肪族、芳香族もしくはヘテロ芳香族有機ラジカル(さらに、1つ以上のH原子はDまたはFにより置きかえられていてもよい)であり、ここで2つ以上の置換基R2は互いに連結されていてもよく、環を形成していてもよく、
Xは、出現する毎に、同一にまたは異なって、任意の所望の脱離基であり、
kは、出現する毎に、同一にまたは異なって、0または1であり、ここでk=ゼロならば、基Eは存在せず、
nは1ないし10の値を有し、
ここで、下記式の化合物
Ar−(X)n
は請求項1に記載のアリール化合物であり、下記式の化合物
- 請求項8に記載の方法であって、全ての基RはH以外であることを特徴とする方法。
- 請求項8または9のいずれか1項に記載の方法であって、窒素原子上の一方または両方の基Rは、前記窒素原子への結合に対してオルト位に置換基を有するアリール基、または前記窒素原子への結合に対してオルト位に縮合環を有するアリール基を表すことを特徴とする方法。
- 請求項8ないし10のいずれか1項に記載の方法であって、nは1または2に等しいことを特徴とする方法。
- 請求項8ないし11のいずれか1項に記載の方法であって、前記基Arは、前記脱離基Xへの結合に対してオルト位に、HおよびD以外である少なくとも1つのラジカルR1を含むことを特徴とする方法。
- 請求項8ないし12のいずれか1項に記載の方法であって、前記基Arはナフタレン、アントラセン、フェナントレン、ピレン、クリセン、ペリレン、フルオランテン、ベンゾアントラセン、ベンゾフェナントレン、テトラセン、ペンタセン、ベンゾピレン、アクリジンおよびフェナントリジンから選択される縮合アリール基を含むか、または前記基Arはフルオレン、スピロビフルオレン、シス−またはトランス−インデノフルオレン、シス−またはトランス−インドロカルバゾール、シス−またはトランス−インデノカルバゾール、シス−またはトランス−モノベンゾインデノフルオレンおよびシス−またはトランス−ジベンゾインデノフルオレンから選択される芳香族環系を含むことを特徴とする方法。
- アミノ化合物とアリール化合物との間の遷移金属で触媒されるカップリング反応における、少なくとも33の、ジメチルスルホキシドに基づくpKa値を有する塩基の使用。
- 請求項14に記載の使用であって、前記塩基は、少なくとも34、好ましくは少なくとも36の、ジメチルスルホキシドに基づくpKa値を有することを特徴とする使用。
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Cited By (2)
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JP2018127451A (ja) * | 2017-02-08 | 2018-08-16 | 国立大学法人岐阜大学 | 芳香族アミン化合物の製造方法と新規な芳香族アミン化合物および蛍光発光材料と紫外線吸収剤 |
JP7193071B2 (ja) | 2017-02-08 | 2022-12-20 | 国立大学法人東海国立大学機構 | 蛍光発光材料および紫外線吸収剤 |
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EP2776386B1 (de) | 2019-11-20 |
WO2013068075A1 (de) | 2013-05-16 |
US20140309458A1 (en) | 2014-10-16 |
US9499474B2 (en) | 2016-11-22 |
EP2776386A1 (de) | 2014-09-17 |
JP6100274B2 (ja) | 2017-03-22 |
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