Copper-Mediated Coupling of 1,1-Dibromo-1-alkenes with Nitrogen Nucleophiles: A General Method for the Synthesis of Ynamides

被引:204
作者
Coste, Alexis [1 ]
Karthikeyan, Ganesan [1 ]
Couty, Francois [1 ]
Evano, Gwilherm [1 ]
机构
[1] Univ Versailles St Quentin Yvelines, Inst Lavoisier Versailles, CNRS, UMR 8180, F-78035 Versailles, France
关键词
copper; cross-coupling; dibromoalkenes; homogeneous catalysis; ynamides; RING-CLOSING METATHESIS; N-FUNCTIONALIZED; 1-ALKYNYLAMIDES; AXIALLY CHIRAL ANILIDES; INTRAMOLECULAR AMIDATION; CATALYZED CYCLIZATION; ALKYNYL BROMIDES; DERIVATIVES; 1,6-DIYNES; CYCLOADDITIONS; CHEMISTRY;
D O I
10.1002/anie.200901099
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Mild reaction conditions are the advantage of the title reaction, which allows straightforward entry to a variety of ynamides starting from readily available 1,1-dibromo-1- alkenes, which act as attractive alkynylating agents (see scheme; EWG=electron-withdrawing group, DMF=N,Ndimethylformamide). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4381 / 4385
页数:5
相关论文
共 75 条
[71]   Copper salt-catalyzed azide-[3+2] cycloadditions of ynamides and bis-ynamides [J].
Zhang, Xuejun ;
Li, Hongyan ;
You, Lingfeng ;
Tang, Yu ;
Hsung, Richard P. .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (16-17) :2437-2442
[72]   Copper(II)-catalyzed amidations of alkynyl bromides as a general synthesis of ynamides and Z-enamides.: An intramolecular amidation for the synthesis of macrocyclic ynamides [J].
Zhang, Xuejun ;
Zhang, Yanshi ;
Huang, Jian ;
Hsung, Richard P. ;
Kurtz, Kimberly C. M. ;
Oppenheimer, Jossian ;
Petersen, Matthew E. ;
Sagamanova, Irina K. ;
Shen, Lichun ;
Tracey, Michael R. .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (11) :4170-4177
[73]   Copper sulfate-pentahydrate-1,10-phenanthroline catalyzed amidations of alkynyl bromides. Synthesis of heteroaromatic amine substituted ynamides [J].
Zhang, YS ;
Hsung, RP ;
Tracey, MR ;
Kurtz, KCM ;
Vera, EL .
ORGANIC LETTERS, 2004, 6 (07) :1151-1154
[74]   Synthesis of Amidines Using N-Allyl Ynamides. A Palladium-Catalyzed Allyl Transfer through an Ynamido-π-Allyl Complex [J].
Zhang, Yu ;
DeKorver, Kyle A. ;
Lohse, Andrew G. ;
Zhang, Yan-Shi ;
Huang, Jian ;
Hsung, Richard P. .
ORGANIC LETTERS, 2009, 11 (04) :899-902
[75]   Recent advances in the chemistry of ynamines and ynamides [J].
Zificsak, CA ;
Mulder, JA ;
Hsung, RP ;
Rameshkumar, C ;
Wei, LL .
TETRAHEDRON, 2001, 57 (36) :7575-7606