Cobalt-catalyzed vinylation of functionalized aryl halides with vinyl acetates

被引:73
作者
Amatore, M [1 ]
Gosmini, C [1 ]
Périchon, J [1 ]
机构
[1] Univ Paris 12, CNRS, UMR 7582, Lab Electrochim Catalyse & Synth Organ, F-94320 Thiais, France
基金
美国国家卫生研究院;
关键词
catalysis; cobalt; cross-coupling; styrene; vinylation;
D O I
10.1002/ejoc.200400897
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new method for the preparation of styrene derivatives is described on the basis of the activation of aryl halides by low-valent cobalt species. A combination of Co-II bromide and 2,2'-bipyridine is suitable as catalyst for the cross-coupling reaction of a wide range of aromatic halides (X = Cl, Br, I), mostly bearing sensitive moieties, with vinyl acetates, These reactions proceed under mild conditions in the presence of the appropriate reducing agent to afford a-substituted styrene compounds in satisfactory to high yields. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim., Germany, 2005).
引用
收藏
页码:989 / 992
页数:4
相关论文
共 27 条
[1]   5-VINYLPYRIMIDINES - SYNTHESIS VIA ORGANOPALLADIUM INTERMEDIATES [J].
ARAI, I ;
DAVES, GD .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1978, 15 (02) :351-352
[2]   PALLADIUM-CATALYZED PHENYLATION OF ENOL ETHERS AND ACETATES [J].
ARAI, I ;
DAVES, GD .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (01) :21-23
[3]   Orthopalladated and -platinated bulky triarylphosphite complexes: Synthesis, reactivity and application as high-activity catalysts for Suzuki and Stille coupling reactions [J].
Bedford, RB ;
Hazlewood, SL ;
Limmert, ME ;
Albisson, DA ;
Draper, SM ;
Scully, PN ;
Coles, SJ ;
Hursthouse, MB .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (14) :3216-3227
[4]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[5]  
Berthiol F, 2003, EUR J ORG CHEM, V2003, P1091
[6]   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
[7]   A HIGHLY-ACTIVE AND STEREOSELECTIVE MONTMORILLONITE CATALYST FOR ARYLATION OF CONJUGATED ALKENES [J].
CHOUDARY, BM ;
SARMA, RM ;
RAO, KK .
TETRAHEDRON, 1992, 48 (04) :719-726
[8]  
Denmark SE, 2000, SYNTHESIS-STUTTGART, P999
[9]   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
[10]  
FILLON H, 2003, Patent No. 03004504