Unexpected tandem Sonogashira-carbopalladation-Sonogashira coupling reaction of benzyl halides with terminal alkynes: A novel four-component domino sequence to highly substituted enynes

被引:22
作者
Pottier, LR [1 ]
Peyrat, JF [1 ]
Alami, M [1 ]
Brion, JD [1 ]
机构
[1] Univ Paris 11, Fac Pharm, CNRS, UMR 8076,BioCIS,Lab Chim Therapeut, F-92296 Chatenay Malabry, France
关键词
Sonogashira; palladium; enynes; benzyl halides; alkynes; four-component coupling;
D O I
10.1055/s-2004-829079
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Unexpected reactivity of benzyl halides with 1-alkynes in Sonogashira reaction promotes in a single-step process the construction of three carbon-carbon bonds regio- and stereoselectively and afforded highly substituted enynes in fair to good yields. The formation of the coupling adduct in this palladium-mediated four-component domino procedure is rationalized by an unprecedented tandem Sonogashira benzylpalladation Sonogashira sequence.
引用
收藏
页码:1503 / 1508
页数:6
相关论文
共 47 条
[1]   Weakly ligated palladium complexes PdCl2(RCN)2 in piperidine:: versatile catalysts for Sonogashira reaction of vinyl chlorides at room temperature [J].
Alami, M ;
Crousse, B ;
Ferri, F .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 624 (1-2) :114-123
[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, 2000, SYNTHESIS-STUTTGART, P1499
[5]   Decelerating effect of alkynes in the oxidative addition of phenyl iodide to palladium(0) complexes in palladium-catalyzed multicomponent reactions and Sonogashira reactions [J].
Amatore, C ;
Bensalem, S ;
Ghalem, S ;
Jutand, A ;
Medjour, Y .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (02) :366-371
[6]   THE PALLADIUM-TRIBUTYLAMMONIUM FORMATE REAGENT IN THE STEREOSELECTIVE HYDROGENATION, AND STEREOSELECTIVE AND REGIOSELECTIVE HYDROARYLATION OF ALKYL 4-HYDROXY-2-ALKYNOATES - A ROUTE TO SUBSTITUTED BUTENOLIDES [J].
ARCADI, A ;
BERNOCCHI, E ;
BURINI, A ;
CACCHI, S ;
MARINELLI, F ;
PIETRONI, B .
TETRAHEDRON, 1988, 44 (02) :481-490
[7]   Carbamoyl-substituted N-heterocyclic carbene complexes of palladium(II):: Application to Sonogashira cross-coupling reactions [J].
Batey, RA ;
Shen, M ;
Lough, AJ .
ORGANIC LETTERS, 2002, 4 (09) :1411-1414
[8]  
Braga AL, 1998, SYNTHESIS-STUTTGART, P39
[9]   Catalytic coupling of terminal acetylenes with iodoarenes and diaryliodonium salts in water [J].
Bumagin, NA ;
Sukhomlinova, LI ;
Luzikova, EV ;
Tolstaya, TP ;
Beletskaya, IP .
TETRAHEDRON LETTERS, 1996, 37 (06) :897-900
[10]   Heterocycles via cyclization of alkynes promoted by organopalladium complexes [J].
Cacchi, S .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :42-64