JP2005513113A5 - - Google Patents
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- JP2005513113A5 JP2005513113A5 JP2003554602A JP2003554602A JP2005513113A5 JP 2005513113 A5 JP2005513113 A5 JP 2005513113A5 JP 2003554602 A JP2003554602 A JP 2003554602A JP 2003554602 A JP2003554602 A JP 2003554602A JP 2005513113 A5 JP2005513113 A5 JP 2005513113A5
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- Japan
- Prior art keywords
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- formula
- alkyl
- ligand
- atom
- Prior art date
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- 238000000034 method Methods 0.000 claims 49
- 239000003446 ligand Substances 0.000 claims 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 20
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 125000000623 heterocyclic group Chemical group 0.000 claims 15
- 230000000269 nucleophilic effect Effects 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000004432 carbon atom Chemical group C* 0.000 claims 11
- 229920006395 saturated elastomer Polymers 0.000 claims 11
- 239000000758 substrate Substances 0.000 claims 11
- 125000001931 aliphatic group Chemical group 0.000 claims 10
- 150000002430 hydrocarbons Chemical group 0.000 claims 10
- 125000002950 monocyclic group Chemical group 0.000 claims 10
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 8
- 125000004429 atom Chemical group 0.000 claims 8
- 229910052751 metal Inorganic materials 0.000 claims 8
- 239000003054 catalyst Substances 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 239000002184 metal Substances 0.000 claims 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims 6
- 125000003367 polycyclic group Chemical group 0.000 claims 6
- 125000002015 acyclic group Chemical group 0.000 claims 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims 5
- 125000002837 carbocyclic group Chemical group 0.000 claims 5
- 238000006243 chemical reaction Methods 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- -1 nioxime Chemical compound 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 125000003277 amino group Chemical group 0.000 claims 4
- 150000001721 carbon Chemical group 0.000 claims 4
- 229910052802 copper Inorganic materials 0.000 claims 4
- 239000010949 copper Substances 0.000 claims 4
- 125000004122 cyclic group Chemical group 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- 125000006539 C12 alkyl 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])C([H])([H])C([H])([H])* 0.000 claims 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 150000002923 oximes Chemical class 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 239000011734 sodium Substances 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 239000011593 sulfur Substances 0.000 claims 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 150000001413 amino acids Chemical class 0.000 claims 2
- 150000001543 aryl boronic acids Chemical class 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 230000003197 catalytic effect Effects 0.000 claims 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 2
- 150000004696 coordination complex Chemical group 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 239000003574 free electron Substances 0.000 claims 2
- 125000000524 functional group Chemical group 0.000 claims 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims 2
- 150000007857 hydrazones Chemical class 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims 2
- 229910052698 phosphorus Inorganic materials 0.000 claims 2
- 239000011591 potassium Substances 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 2
- 229910052725 zinc Inorganic materials 0.000 claims 2
- 239000011701 zinc Substances 0.000 claims 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 claims 1
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims 1
- MUUAQFJJUGVBGB-UHFFFAOYSA-N 1-bromo-2,3,4-trifluorobenzene Chemical group FC1=CC=C(Br)C(F)=C1F MUUAQFJJUGVBGB-UHFFFAOYSA-N 0.000 claims 1
- VEUMANXWQDHAJV-UHFFFAOYSA-N 2-[2-[(2-hydroxyphenyl)methylideneamino]ethyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCN=CC1=CC=CC=C1O VEUMANXWQDHAJV-UHFFFAOYSA-N 0.000 claims 1
- HELKFYIVNMKWJJ-UHFFFAOYSA-N 2-cyanopropanedioic acid Chemical compound OC(=O)C(C#N)C(O)=O HELKFYIVNMKWJJ-UHFFFAOYSA-N 0.000 claims 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims 1
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 claims 1
- QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-UHFFFAOYSA-N 0.000 claims 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical class CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims 1
- YMOONIIMQBGTDU-VOTSOKGWSA-N [(e)-2-bromoethenyl]benzene Chemical compound Br\C=C\C1=CC=CC=C1 YMOONIIMQBGTDU-VOTSOKGWSA-N 0.000 claims 1
- SBYMUDUGTIKLCR-VOTSOKGWSA-N [(e)-2-chloroethenyl]benzene Chemical compound Cl\C=C\C1=CC=CC=C1 SBYMUDUGTIKLCR-VOTSOKGWSA-N 0.000 claims 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims 1
- 150000008046 alkali metal hydrides Chemical class 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 150000001345 alkine derivatives Chemical class 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 238000006254 arylation reaction Methods 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims 1
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Inorganic materials [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 claims 1
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 1
- 125000005620 boronic acid group Chemical group 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims 1
- 229910000024 caesium carbonate Inorganic materials 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 229910000019 calcium carbonate Inorganic materials 0.000 claims 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 1
- 238000003763 carbonization Methods 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229910017052 cobalt Inorganic materials 0.000 claims 1
- 239000010941 cobalt Substances 0.000 claims 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 1
- BLRXYTIIKIPJQL-UHFFFAOYSA-N dicarbide(1-) Chemical compound [C-]#C BLRXYTIIKIPJQL-UHFFFAOYSA-N 0.000 claims 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 150000004679 hydroxides Chemical class 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000000879 imine group Chemical group 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 239000002370 magnesium bicarbonate Substances 0.000 claims 1
- 235000014824 magnesium bicarbonate Nutrition 0.000 claims 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 claims 1
- 239000001095 magnesium carbonate Substances 0.000 claims 1
- IFYDWYVPVAMGRO-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]tetradecanamide Chemical compound CCCCCCCCCCCCCC(=O)NCCCN(C)C IFYDWYVPVAMGRO-UHFFFAOYSA-N 0.000 claims 1
- DNYZBFWKVMKMRM-UHFFFAOYSA-N n-benzhydrylidenehydroxylamine Chemical compound C=1C=CC=CC=1C(=NO)C1=CC=CC=C1 DNYZBFWKVMKMRM-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 150000002828 nitro derivatives Chemical class 0.000 claims 1
- 150000005677 organic carbonates Chemical class 0.000 claims 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 1
- 125000000160 oxazolidinyl group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 230000000737 periodic effect Effects 0.000 claims 1
- 125000004437 phosphorous atom Chemical group 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- 229910052709 silver Inorganic materials 0.000 claims 1
- 239000004332 silver Substances 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 229910000104 sodium hydride Inorganic materials 0.000 claims 1
- 239000012312 sodium hydride Substances 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims 1
- 125000002130 sulfonic acid ester group Chemical group 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- 150000003536 tetrazoles Chemical class 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 150000003852 triazoles Chemical class 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 150000003672 ureas Chemical class 0.000 claims 1
- 238000006886 vinylation reaction Methods 0.000 claims 1
- 0 CC*(C)(C)N(C)C(*)[Rh] Chemical compound CC*(C)(C)N(C)C(*)[Rh] 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0116547A FR2833947B1 (fr) | 2001-12-20 | 2001-12-20 | Procede d'arylation ou de vinylation d'un compose nucleophile |
| PCT/FR2002/004499 WO2003053885A1 (fr) | 2001-12-20 | 2002-12-20 | Procede de formation d'une liaison carbone-carbone ou carbone-heteroatome. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005513113A JP2005513113A (ja) | 2005-05-12 |
| JP2005513113A5 true JP2005513113A5 (enExample) | 2006-02-02 |
Family
ID=8870744
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003554602A Pending JP2005513113A (ja) | 2001-12-20 | 2002-12-20 | 炭素−炭素結合または炭素−ヘテロ原子結合を形成するための方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US6960665B2 (enExample) |
| EP (1) | EP1456151A1 (enExample) |
| JP (1) | JP2005513113A (enExample) |
| CN (1) | CN1615284A (enExample) |
| AU (1) | AU2002364478A1 (enExample) |
| CA (1) | CA2470141A1 (enExample) |
| FR (1) | FR2833947B1 (enExample) |
| WO (1) | WO2003053885A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1863752A (zh) * | 2002-08-02 | 2006-11-15 | 罗迪亚药业公司 | 铜催化的芳基化 |
| FR2859205B1 (fr) * | 2003-08-28 | 2006-02-03 | Rhodia Chimie Sa | Procede de formation d'une liaison carbone-carbone ou carbone-heteroatome |
| JP2006342127A (ja) * | 2005-06-10 | 2006-12-21 | Koei Chem Co Ltd | アリールピラゾール類の製造法 |
| US9162953B2 (en) * | 2006-07-05 | 2015-10-20 | Centre Nationale De Recherche Scientifique | Iron-copper co-catalyzed process for carbon-carbon or carbon-heteroatom bonding |
| FR2915200B1 (fr) | 2007-04-20 | 2009-07-03 | Centre Nat Rech Scient | Procede de preparation de ligands de type phosphines butadieniques,leurs complexes avec le cuivre,et leurs applications en catalyse |
| US9272274B2 (en) | 2007-12-06 | 2016-03-01 | Centre National De La Recherche Scientifique (C.N.R.S.) | Catalytic system for cross-coupling reactions |
| JP5539162B2 (ja) * | 2010-11-04 | 2014-07-02 | キヤノン株式会社 | エレクトロクロミック素子 |
| CN102432523B (zh) * | 2011-09-21 | 2013-11-06 | 温州大学 | 一种3-羟基-3-芳基吲哚-2-酮衍生物的合成方法 |
| CN106083901A (zh) * | 2016-06-03 | 2016-11-09 | 合肥工业大学 | 一种铜配合物 |
| CN109134375A (zh) * | 2018-10-22 | 2019-01-04 | 江苏长青农化股份有限公司 | 一种氟虫腈的制备方法 |
| CN112574135B (zh) * | 2020-12-14 | 2022-09-23 | 湖南工程学院 | 4-芳基-5-硫醚基-2-二氟甲基恶唑及其衍生物及合成方法 |
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2001
- 2001-12-20 FR FR0116547A patent/FR2833947B1/fr not_active Expired - Fee Related
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2002
- 2002-05-31 US US10/159,506 patent/US6960665B2/en not_active Expired - Fee Related
- 2002-12-20 JP JP2003554602A patent/JP2005513113A/ja active Pending
- 2002-12-20 CN CNA028273362A patent/CN1615284A/zh active Pending
- 2002-12-20 EP EP02799841A patent/EP1456151A1/fr active Pending
- 2002-12-20 CA CA002470141A patent/CA2470141A1/fr not_active Abandoned
- 2002-12-20 US US10/499,453 patent/US20050065350A1/en not_active Abandoned
- 2002-12-20 AU AU2002364478A patent/AU2002364478A1/en not_active Abandoned
- 2002-12-20 WO PCT/FR2002/004499 patent/WO2003053885A1/fr not_active Ceased
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