Visible-light-mediated addition of α-aminoalkyl radicals generated from α-silylamines to α,β-unsaturated carbonyl compounds

被引：117

作者：

Miyake, Yoshihiro ^{[1
]}

Ashida, Yuya ^{[1
]}

Nakajima, Kazunari ^{[1
]}

Nishibayashi, Yoshiaki ^{[1
]}

机构：

[1] Univ Tokyo, Sch Engn, Inst Engn Innovat, Bunkyo Ku, Tokyo 1138656, Japan

来源：

CHEMICAL COMMUNICATIONS | 2012年 / 48卷 / 55期

关键词：

PHOTOINDUCED ELECTRON-TRANSFER; PHOTOREDOX CATALYSIS; TRANSFER PHOTOCHEMISTRY; CYCLIZATION REACTIONS; OXIDATION POTENTIALS; HYDROGEN-PRODUCTION; PRACTICAL METHOD; TERTIARY-AMINES; METAL-COMPLEXES; CATION RADICALS;

D O I：

10.1039/c2cc32745g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Visible-light-mediated addition of alpha-aminoalkyl radicals generated from alpha-silylamines to alpha,beta-unsaturated carbonyl compounds using a photoredox catalyst is developed. We also succeeded in the isolation of a silyl enol ether as a primary product of the photochemical reaction.

引用

页码：6966 / 6968

页数：3

共 51 条

[1] Barrier to enantiomerization of unstabilized, chelated, and dipole-stabilized 2-lithiopyrrolidines [J].

Ashweek, NJ ;

Brandt, P ;

Coldham, I ;

Dufour, S ;

Gawley, RE ;

Hæffner, F ;

Klein, R ;

Sanchez-Jimenez, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (01) :449-457

[2] Recent developments in cyclization reactions of α-aminoalkyl radicals [J].

Aurrecoechea, JM ;

Suero, R .

ARKIVOC, 2004, :10-35

[3] Catalytic enantioselective reactions driven by photoinduced electron transfer [J].

Bauer, A ;

Westkämper, F ;

Grimme, S ;

Bach, T .

NATURE, 2005, 436 (7054) :1139-1140

[4] Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp3-Hybridized C-H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides [J].

Bellina, Fabio ;

Rossi, Renzo .

CHEMICAL REVIEWS, 2010, 110 (02) :1082-1146

[5] PHOTO-OXIDATION OF SOME CARBINOLS BY THE RU(II) POLYPYRIDYL COMPLEX ARYL DIAZONIUM SALT SYSTEM [J].

CANOYELO, H ;

DERONZIER, A .

TETRAHEDRON LETTERS, 1984, 25 (48) :5517-5520

[6] Studies Leading to the Development of a Single-Electron Transfer (SET) Photochemical Strategy for Syntheses of Macrocyclic Polyethers, Polythioethers, and Polyamides [J].

Cho, Dae Won ;

Yoon, Ung Chan ;

Mariano, Patrick S. .

ACCOUNTS OF CHEMICAL RESEARCH, 2011, 44 (03) :204-215

[7] Homogeneous Catalytic System for Photoinduced Hydrogen Production Utilizing Iridium and Rhodium Complexes [J].

Cline, Eric D. ;

Adamson, Samantha E. ;

Bernhard, Stefan .

INORGANIC CHEMISTRY, 2008, 47 (22) :10378-10388

[8] SILICON-CARBON HYPERCONJUGATION IN CATION RADICALS .1. LOWERING OF OXIDATION POTENTIALS OF N-[(TRIMETHYLSILYL)METHYL] AROMATIC AMINES [J].

COOPER, BE ;

OWEN, WJ .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1971, 29 (01) :33-&

[9] PHOTOINDUCED ELECTRON-TRANSFER REACTIONS OF TRANSITION-METAL COMPLEXES WITH AMINES - MECHANISTIC STUDIES OF ALTERNATE PATHWAYS TO BACK ELECTRON-TRANSFER [J].

DELAIVE, PJ ;

FOREMAN, TK ;

GIANNOTTI, C ;

WHITTEN, DG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (17) :5627-5631

[10] Highly efficient photocatalytic oxygenation reactions using water as an oxygen source [J].

Fukuzumi, Shunichi ;

Kishi, Takashi ;

Kotani, Hiroaki ;

Lee, Yong-Min ;

Nam, Wonwoo .

NATURE CHEMISTRY, 2011, 3 (01) :38-41

← 1 2 3 4 5 6 →