Aryl Radical Formation by Copper(I) Photocatalyzed Reduction of Diaryliodonium Salts: NMR Evidence for a CuII/CuI Mechanism

被引:140
作者
Baralle, Alexandre [1 ]
Fensterbank, Louis [1 ]
Goddard, Jean-Philippe [1 ]
Ollivier, Cyril [1 ]
机构
[1] Sorbonne Univ, Univ Paris 06, Inst Parisien Chim Mol, UMR CNRS 7201, 4 Pl Jussieu,C 229, F-75005 Paris, France
关键词
allylation; copper; iodonium; photocatalysis; radical reactions; LIGHT PHOTOREDOX CATALYSIS; VISIBLE-LIGHT; ELECTRON-TRANSFER; DIAZONIUM SALTS; H ARYLATION; COORDINATION-COMPOUNDS; SYNTHETIC APPLICATIONS; CARBONYL-COMPOUNDS; POLYVALENT IODINE; ARYLBORONIC ACIDS;
D O I
10.1002/chem.201301449
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Photocatalyzed reduction of diaryliodonium salts was achieved by using [Cu(dpp)2][PF6] as a photoactive complex and DIPEA as a reductive quench. The application of a copper catalyst allows the generation of aryl radicals under mild conditions and maintains their reactivity for C-C bond formation processes. © 2013 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:10809 / 10813
页数:5
相关论文
共 100 条
[1]  
Andrews R.S., 2010, ANGEW CHEM, V122, P7432
[2]   A Photoflow Reactor for the Continuous Photoredox-Mediated Synthesis of C-Glycoamino Acids and C-Glycolipids [J].
Andrews, R. Stephen ;
Becker, Jennifer J. ;
Gagne, Michel R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (17) :4140-4143
[3]   Investigating the Rate of Photoreductive Glucosyl Radical Generation [J].
Andrews, R. Stephen ;
Becker, Jennifer J. ;
Gagne, Michel R. .
ORGANIC LETTERS, 2011, 13 (09) :2406-2409
[4]   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
[5]  
[Anonymous], 2012, ANGEW CHEM
[6]   Photochemistry and photophysics of coordination compounds: Copper [J].
Armaroli, Nicola ;
Accorsi, Gianluca ;
Cardinali, Francois ;
Listorti, Andrea .
PHOTOCHEMISTRY AND PHOTOPHYSICS OF COORDINATION COMPOUNDS I, 2007, 280 :69-115
[7]   Visible-light-mediated photochemistry: accelerating Ru(bpy)32+-catalyzed reactions in continuous flow [J].
Bou-Hamdan, Farhan R. ;
Seeberger, Peter H. .
CHEMICAL SCIENCE, 2012, 3 (05) :1612-1616
[8]   Synthesis using aromatic homolytic substitution - recent advances [J].
Bowman, W. Russell ;
Storey, John M. D. .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (11) :1803-1822
[9]   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
[10]   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