Copper-Catalyzed Cross-Coupling of Alkyl and Aryl Grignard Reagents with Alkynyl Halides

被引:96
作者
Cahiez, Gerard [1 ]
Gager, Olivier [1 ]
Buendia, Julien [1 ]
机构
[1] Univ Paris 13, Dept Chem FRE 3043, CNRS, F-93017 Bobigny, France
关键词
alkynes; copper; cross-coupling; Grignard reagents; VINYL ORGANOCOPPER COMPOUNDS; STEREOSPECIFIC SYNTHESIS; DERIVATIVES; BROMIDES; ACIDS; CARBONATION; 1-ALKYNES; IODIDES;
D O I
10.1002/anie.200905816
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Good old copperl A new general procedure to couple aliphatic and aromatic Grignard reagents with alkynyl halides under copper catalysis is described (see scheme; NMP=N-methylpyrrolidinone). The reaction is chemoselective and allows preparation of a vast array of simple and functionalized internal alkynes in high yields. © 2010 Wiley-VCH Verlag GmbH &. Co. KCaA.
引用
收藏
页码:1278 / 1281
页数:4
相关论文
共 37 条
[1]   The first palladium-catalyzed Sonogashira coupling of unactivated secondary alkyl bromides [J].
Altenhoff, G ;
Würtz, S ;
Glorius, F .
TETRAHEDRON LETTERS, 2006, 47 (17) :2925-2928
[2]   STUDIES WITH ACETYLENES .1. SOME REACTIONS OF GRIGNARD REAGENTS WITH ALK-1-YNYL AND ALK-1-ENYL HALIDES [J].
BLACK, HK ;
HORN, DHS ;
WEEDON, BCL .
JOURNAL OF THE CHEMICAL SOCIETY, 1954, (JUN) :1704-1709
[3]  
Boymond L, 1998, ANGEW CHEM INT EDIT, V37, P1701, DOI 10.1002/(SICI)1521-3773(19980703)37:12<1701::AID-ANIE1701>3.0.CO
[4]  
2-U
[5]  
Boymond L., 1998, ANGEW CHEM, V110, P1801
[6]  
BRANDSMA L, 1988, PREPARATIVE ACETYLEN, P39
[7]   Alkylation of 1-alkynes in THF [J].
Buck, M ;
Chong, JM .
TETRAHEDRON LETTERS, 2001, 42 (34) :5825-5827
[8]   Cu-catalyzed alkylation of Grignard reagents:: A new efficient procedure [J].
Cahiez, G ;
Chaboche, C ;
Jézéquel, M .
TETRAHEDRON, 2000, 56 (18) :2733-2737
[9]   Cu-catalyzed alkylation and Fe-catalyzed alkenylation of organomanganese reagents [J].
Cahiez, G ;
Marquais, S .
PURE AND APPLIED CHEMISTRY, 1996, 68 (01) :53-60
[10]  
CAHIEZ G, 1993, SYNLETT, P45