Weakly ligated palladium complexes PdCl2(RCN)2 in piperidine:: versatile catalysts for Sonogashira reaction of vinyl chlorides at room temperature

被引:89
作者
Alami, M [1 ]
Crousse, B [1 ]
Ferri, F [1 ]
机构
[1] Fac Pharm, Lab Chim Therapeut Associe CNRS, UPRESA 8076, BIOCIS, F-92296 Chatenay Malabry, France
关键词
palladium; copper; amino vinyl chlorides; amino enynes; terbinafine;
D O I
10.1016/S0022-328X(00)00909-8
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Copper iodide and weakly ligated palladium complexes PdCl2(RCN)(2) (R = Ph, Me) catalyzed efficiently the coupling reaction of vinyl chlorides with 1-alkynes in the presence of piperidine to give the corresponding conjugated enynes in good to excellent yields. The reaction takes place rapidly and cleanly at room temperature. Application to the synthesis of terbinafine which exhibits strong antimycotic activity has been realized. (C) 2001 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:114 / 123
页数:10
相关论文
共 52 条
[1]   A two-step synthesis of terbinafine [J].
Alami, M ;
Ferri, F ;
Gaslain, Y .
TETRAHEDRON LETTERS, 1996, 37 (01) :57-58
[2]   AN EFFICIENT PALLADIUM-CATALYZED REACTION OF VINYL AND ARYL HALIDES OR TRIFLATES WITH TERMINAL ALKYNES [J].
ALAMI, M ;
FERRI, F ;
LINSTRUMELLE, G .
TETRAHEDRON LETTERS, 1993, 34 (40) :6403-6406
[3]   AN EFFICIENT PALLADIUM-CATALYZED REACTION OF VINYL CHLORIDES WITH TERMINAL ACETYLENES [J].
ALAMI, M ;
LINSTRUMELLE, G .
TETRAHEDRON LETTERS, 1991, 32 (43) :6109-6112
[4]  
Alami M, 1998, SYNLETT, P325
[5]  
Alami M, 2000, SYNTHESIS-STUTTGART, P1499
[6]  
ALAMI M, 1999, ACROS ORGANICS ACTA, V6, P13
[7]   VINYL ORGANOCOPPER COMPOUNDS .9. ADDITION OF ORGANIC COPPER DERIVATIVES TO ACETYLENE [J].
ALEXAKIS, A ;
CAHIEZ, G ;
NORMANT, JF .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1979, 177 (01) :293-298
[8]  
Braga AL, 1998, SYNTHESIS-STUTTGART, P39
[9]  
Brandsma L., 1998, APPL TRANSITION META
[10]   The first and convenient synthesis of acyclic dienediynes related to neocarzinostatin chromophore [J].
Bujard, M ;
Ferri, F ;
Alami, M .
TETRAHEDRON LETTERS, 1998, 39 (24) :4243-4246