Manganese-Catalyzed Oxidative Cross-Coupling of Grignard Reagents with Oxygen as an Oxidant

被引:55
作者
Cahiez, Gerard [1 ]
Duplais, Christophe [1 ]
Buendia, Julien [1 ]
机构
[1] Univ Paris 13, CNRS, Dept Chem, F-93017 Bobigny, France
关键词
cross-coupling; Grignard reagents; manganese; oxidation; synthetic methods; REDUCTIVE ELIMINATION; ORGANOMANGANESE REAGENTS; ORGANOMAGNESIUM REAGENTS; HETEROCYCLIC CHLORIDES; BIARYL SYNTHESIS; ALKENYL HALIDES; ARYL HALIDES; COMPLEXES; ARYLATION; KETONES;
D O I
10.1002/anie.200902188
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Oxidative heterocoupling between two Grignard reagents RMgX and R′MgX is made possible by manganese catalysis with O2 as an oxidant. This procedure, development of which was based on mechanistic analysis of the corresponding homocoupling reaction, can be steered towards the heterocoupling product at the expense of the homocoupling products by judicious choice of the R and R′ groups (see examples). © 2009 Wiley-VCH Verlag GmbH & Co. KCaA.
引用
收藏
页码:6731 / 6734
页数:4
相关论文
共 55 条
[31]   Mechanistic studies of ligand-induced thermolytic reductive elimination of biaryl from tetraarylosmium(IV) [J].
Hardy, DT ;
Wilkinson, G ;
Young, GB .
POLYHEDRON, 1996, 15 (08) :1363-1373
[32]   Aryl-aryl bond formation one century after the discovery of the Ullmann reaction [J].
Hassan, J ;
Sévignon, M ;
Gozzi, C ;
Schulz, E ;
Lemaire, M .
CHEMICAL REVIEWS, 2002, 102 (05) :1359-1469
[33]   Catalytic and highly regioselective cross-coupling of aromatic C-H substrates [J].
Hull, Karni L. ;
Sanford, Melanie S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (39) :11904-+
[34]   Oxidative C-H activation/C-C bond forming reactions: Synthetic scope and mechanistic insights [J].
Kalyani, D ;
Deprez, NR ;
Desai, LV ;
Sanford, MS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (20) :7330-7331
[35]  
Kantchev E.A. B., 2007, ANGEW CHEM, V119, P2824
[36]   Palladium complexes of N-heterocyclic carbenes as catalysts for cross-coupling reactions - A synthetic chemist's perspective [J].
Kantchev, Eric Assen B. ;
O'Brien, Christopher J. ;
Organ, Michael G. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (16) :2768-2813
[37]  
Korn TJ, 2003, SYNLETT, P1892
[38]   Cobalt-catalyzed cross-coupling reactions of heterocyclic chlorides with arylmagnesium halides and of polyfunctionalized arylcopper reagents with aryl bromides, chlorides, fluorides and tosylates [J].
Korn, Tobias J. ;
Schade, Matthias A. ;
Cheemala, Murthy N. ;
Wirth, Stefan ;
Guevara, Simon A. ;
Cahiez, Gerard ;
Knochel, Paul .
SYNTHESIS-STUTTGART, 2006, (21) :3547-3574
[39]   Palladium-catalyzed benzene arylation: Incorporation of catalytic pivalic acid as a proton shuttle and a key element in catalyst design [J].
Lafrance, Marc ;
Fagnou, Keith .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (51) :16496-16497
[40]   Intramolecular Pd(II)-catalyzed oxidative biaryl synthesis under air:: Reaction development and scope [J].
Liegault, Benoit ;
Lee, Doris ;
Huestis, Malcolm P. ;
Stuart, David R. ;
Fagnou, Keith .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (13) :5022-5028