Palladium-catalyzed Suzuki-Miyaura coupling reactions involving β,β-dihaloenamides:: Application to the synthesis of disubstituted ynamides

被引:47
|
作者
Couty, S [1 ]
Barbazanges, M [1 ]
Meyer, C [1 ]
Cossy, J [1 ]
机构
[1] Ecole Super Phys & Chim Ind Ville Paris, Assoc CNRS, Chim Organ Lab, F-75231 Paris, France
关键词
cross-coupling; palladium; enamides; eliminations; ynamides;
D O I
10.1055/s-2005-864821
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
beta,beta-Dihaloenamides can be successfully involved in palladium-catalyzed Suzuki-Miyaura coupling reactions. Whereas the resulting trisubstituted (Z)-beta-bromoenamides could participate in a second cross-coupling leading to beta, beta-disubstituted enamides, the (Z)-beta-chloroenamides have been converted to disubstituted ynamides by an E-2 elimination.
引用
收藏
页码:905 / 910
页数:6
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