Arenediazonium o-benzenedisulfonimides as efficient reagents for Heck-type arylation reactions

被引：60
作者：
Artuso, E [1 ]
Barbero, M [1 ]
Degani, I [1 ]
Dughera, S [1 ]
Fochi, R [1 ]
机构：
[1] Univ Turin, Dipartimento Chim Gen & Organ Applicata, I-10125 Turin, Italy
来源：
TETRAHEDRON | 2006年 / 62卷 / 13期
关键词：
dry diazonium salts; Pd-catalyzed reactions; Heck; arylation;
D O I：
10.1016/j.tet.2006.01.027
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Arenediazonium o-benzenedisulfonimides can be used as new and efficient reagents for Heck-type arylation reactions of sonic common substrates containing C-C multiple bonds, namely ethyl acrylate, acrylic acid, acroleyne. styrene and cyclopentene, The reactions were carried out in an organic solvent, in the presence of Pd(OAc)(2) as pre-catalyst, and gave rise to arylated products, for example, ethyl cinnaniates, cinnamic acids. cinnamic aldehydes and stilbenes, possessing an (E)-configuration, and 1-arylcyclopentenes, in good to excellent yields. It is noteworthy that all the reactions led to the recovery, in greater than 80% yield, of o-benzenedisulfonimide, recyclable for the preparation of other diazonium salts. (c) 2006 Elsevier Ltd. All rights reserved.
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收藏
页码：3146 / 3157
页数：12
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