2,2′-bipyridine:: An efficient ligand in the cobalt-catalyzed synthesis of organozinc reagents from aryl chlorides and sulfonates

被引:40
作者
Kazmierski, I
Gosmini, C
Paris, JM
Périchon, J
机构
[1] Univ Paris 12, CNRS, Lab Electrochim Catalyse & Synth Organ, UMR 7582, F-94320 Thiais, France
[2] Rhodia, Res Ctr Lyon, F-69192 St Fons, France
关键词
cobalt halide; catalysis; zinc; aromatic chlorides; triflates;
D O I
10.1055/s-2006-939060
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of functionalized arylzinc reagents from aromatic chlorides, triflates, or mesylates, via cobalt catalysis, is reported using 2,2'-bipyridine as a ligand in a mixture of acetonitrile and pyridine. This procedure allows the synthesis of a variety of functionalized arylzinc species in good to excellent yields. Some of these arylzinc compounds have been coupled with aromatic bromides under palladium catalysis.
引用
收藏
页码:881 / 884
页数:4
相关论文
共 31 条
[1]   Oxidative addition of C-CN bond to nickel(0) complex: Synthesis and crystal structures of Ni(CN)(o-C6H4CN)(bpy) and Ni(CN) (p-C6H4CN)(bpy) [J].
Abla, M ;
Yamamoto, T .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 532 (1-2) :267-270
[2]   Cobalt-catalyzed vinylation of functionalized aryl halides with vinyl acetates [J].
Amatore, M ;
Gosmini, C ;
Périchon, J .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (06) :989-992
[3]   Stability and reactivity of electrogenerated cobalt(I) towards aryl halides in the presence of additives such as vinyl acetate or methyl vinyl ketone -: Application to the electrosynthesis of arylzinc compounds [J].
Buriez, O ;
Nédélec, JY ;
Périchon, J .
JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 2001, 506 (02) :162-169
[4]   New chemical synthesis of functionalized arylzinc compounds from aromatic or thienyl bromides under mild conditions using a simple cobalt catalyst and zinc dust [J].
Fillon, H ;
Gosmini, C ;
Périchon, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (13) :3867-3870
[5]   Electrosynthesis of functionalized organodizinc compounds from aromatic dihalides via a cobalt catalysis in acetonitrile/pyridine as solvent [J].
Fillon, H ;
Gosmini, C ;
Nédélec, JY ;
Périchon, J .
TETRAHEDRON LETTERS, 2001, 42 (23) :3843-3846
[6]   Cleavage of carbon-carbon bonds in aromatic nitriles using nickel(0) [J].
Garcia, JJ ;
Brunkan, NM ;
Jones, WD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (32) :9547-9555
[7]   New efficient preparation of functionalized arylzinc or thienylzinc compounds from aryl or thienyl chlorides using cobalt catalysis [J].
Gosmini, C ;
Amatore, M ;
Claudel, S ;
Périchon, J .
SYNLETT, 2005, (14) :2171-2174
[8]   New efficient preparation of arylzinc compounds from aryl halides using cobalt catalysis and sacrificial anode process [J].
Gosmini, C ;
Rollin, Y ;
Nédélec, JY ;
Périchon, J .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) :6024-6026
[9]  
GOSMINI C, 2000, Patent No. 0102626
[10]   New progress in the cobalt-catalysed synthesis of aromatic organozinc compounds by reduction of aromatic halides by zinc dust [J].
Kazmierski, I ;
Gosmini, C ;
Paris, JM ;
Périchon, J .
TETRAHEDRON LETTERS, 2003, 44 (34) :6417-6420