Oxyarylation and Aminoarylation of Styrenes Using Photoredox Catalysis

被引:159
作者
Fumagalli, Gabriela [1 ]
Boyd, Scott [2 ]
Greaney, Michael F. [1 ]
机构
[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England
[2] AstraZeneca, Macclesfield SK10 4TG, Cheshire, England
基金
英国工程与自然科学研究理事会;
关键词
VISIBLE-LIGHT PHOTOREDOX; C-H ARYLATION; ARYL DIAZONIUM; ARYLBORONIC ACIDS; HIGHLY EFFICIENT; ALPHA-ARYLATION; METAL-FREE; ALKENES; GOLD; PHOTOCATALYSIS;
D O I
10.1021/ol401940c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A three-component coupling of styrenes is reported, using photoredox catalysis to achieve simultaneous arylation and C-O or C-N bond formation across the styrene double bond.
引用
收藏
页码:4398 / 4401
页数:4
相关论文
共 51 条
[1]  
[Anonymous], J CHEM SOC REV
[2]   Gold-Catalysed Oxyarylation of Styrenes and Mono- and gem-Disubstituted Olefins Facilitated by an Iodine(III) Oxidant [J].
Ball, Liam T. ;
Lloyd-Jones, Guy C. ;
Russell, Christopher A. .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (10) :2931-2937
[3]   Arylsilanes: Application to Gold-Catalyzed Oxyarylation of Alkenes [J].
Ball, Liam T. ;
Green, Michael ;
Lloyd-Jones, Guy C. ;
Russell, Christopher A. .
ORGANIC LETTERS, 2010, 12 (21) :4724-4727
[4]   Regiospecific one-pot synthesis of diaryliodonium tetrafluoroborates from arylboronic acids and aryl iodides [J].
Bielawski, Marcin ;
Aili, David ;
Olofsson, Berit .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (12) :4602-4607
[5]   Aryl Diazonium versus Iodonium Salts: Preparation, Applications and Mechanisms for the Suzuki-Miyaura Cross-Coupling Reaction [J].
Bonin, Helene ;
Fouquet, Eric ;
Felpin, Francois-Xavier .
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (17) :3063-3084
[6]   Visible-Light-Promoted C-C Bond Cleavage: Photocatalytic Generation of Iminium Ions and Amino Radicals [J].
Cai, Shunyou ;
Zhao, Xinyang ;
Wang, Xinbo ;
Liu, Qisong ;
Li, Zigang ;
Wang, David Zhigang .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (32) :8050-8053
[7]   PHOTOCATALYSIS OF THE PSCHORR REACTION BY TRIS-(2,2'-BIPYRIDYL)RUTHENIUM(II) IN THE PHENANTHRENE SERIES [J].
CANOYELO, H ;
DERONZIER, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1984, (06) :1093-1098
[8]   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
[9]   PHOTO-OXIDATION OF TRIS(2,2'-BIPYRIDINE)RUTHENIUM(II) BY PARA-SUBSTITUTED BENZENE DIAZONIUM SALTS IN ACETONITRILE 2-COMPARTMENT PHOTOELECTROCHEMICAL CELL APPLICATIONS [J].
CANOYELO, H ;
DERONZIER, A .
JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS I, 1984, 80 :3011-3019
[10]   Tandem Cyclizations of 1,6-Enynes with Arylsulfonyl Chlorides by Using Visible-Light Photoredox Catalysis [J].
Deng, Guo-Bo ;
Wang, Zhi-Qiang ;
Xia, Jia-Dong ;
Qian, Peng-Cheng ;
Song, Ren-Jie ;
Hu, Ming ;
Gong, Lu-Bin ;
Li, Jin-Heng .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (05) :1535-1538