The Reaction of Tertiary Anilines with Maleimides under Visible Light Redox Catalysis

被引:135
作者
Ju, Xuhui [1 ]
Li, Dianjun [1 ]
Li, Weifei [1 ]
Yu, Wei [1 ]
Bian, Fengling [1 ]
机构
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
关键词
aerobic oxidation; maleimides; photocatalysis; tertiary anilines; tetrahydroquinolines; C-H FUNCTIONALIZATION; ELECTRON-TRANSFER PET; PHOTOREDOX CATALYSIS; SYNTHETIC APPLICATIONS; CYCLIZATION REACTIONS; COUPLING REACTION; MOLECULAR-OXYGEN; BOND FORMATION; AMINES; PHOTOCATALYSIS;
D O I
10.1002/adsc.201200608
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Tertiary anilines can be prompted to react with N-aryl- and N-benzylmaleimides to form tetrahydroquinoline products under photocatalysis using visible light irradiation, the ruthenium or iridium complexes Ru(bpy)3Cl2 or Ir(ppy)2(dtbbpy)PF6 as catalyst, and air as terminal oxidant.
引用
收藏
页码:3561 / 3567
页数:7
相关论文
共 61 条
[1]  
Andrews R.S., 2010, ANGEW CHEM, V122, P7432
[2]   Intermolecular Addition of Glycosyl Halides to Alkenes Mediated by Visible Light [J].
Andrews, R. Stephen ;
Becker, Jennifer J. ;
Gagne, Michel R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (40) :7274-7276
[3]   Kinetic deuterium isotope effect profiles and substituent effects in the oxidative N-demethylation of N,N-dimethylanilines catalyzed by tetrakis(pentafluorophenyl)porphyrin iron(III) chloride [J].
Baciocchi, E ;
Lanzalunga, O ;
Lapi, A ;
Manduchi, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (23) :5783-5787
[4]   Diastereoselective tandem addition-cyclization reactions of unsaturated tertiary amines initiated by photochemical electron transfer (PET) [J].
Bertrand, S ;
Hoffmann, N ;
Humbel, S ;
Pete, JP .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (25) :8690-8703
[5]   Visible-Light Photoredox Catalysis: Aza-Henry Reactions via C-H Functionalization [J].
Condie, Allison G. ;
Gonzalez-Gomez, Jose C. ;
Stephenson, Corey R. J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (05) :1464-+
[6]   Generation of ketyl radical anions by photoinduced electron transfer (PET) between ketones and amines. Synthetic applications [J].
Cossy, Janine ;
Belotti, Damien .
TETRAHEDRON, 2006, 62 (27) :6459-6470
[7]   Visible-light-mediated conversion of alcohols to halides [J].
Dai, Chunhui ;
Narayanam, Jagan M. R. ;
Stephenson, Corey R. J. .
NATURE CHEMISTRY, 2011, 3 (02) :140-145
[8]   CONCERNING USE OF AMINES AS PROBES FOR PARTICIPATION OF SINGLET OXYGEN IN DYE-SENSITIZED OXYGENATION REACTIONS [J].
DAVIDSON, RS ;
TRETHEWEY, KR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1977, (02) :178-182
[9]   PHOTOSENSITIZED OXIDATION OF AMINES - MECHANISM OF OXIDATION OF TRIETHYLAMINE [J].
DAVIDSON, RS ;
TRETHEWEY, KR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1977, (02) :173-178
[10]   ENERGY-TRANSFER FROM LUMINESCENT TRANSITION-METAL COMPLEXES TO OXYGEN [J].
DEMAS, JN ;
HARRIS, EW ;
MCBRIDE, RP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (11) :3547-3551