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.

引用

页码：3146 / 3157

页数：12

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