Azidosubstituted arylboronic acids: synthesis and Suzuki-Miyaura cross-coupling reactions

被引：12
|
作者：
Sviridov, SI
Vasi'ev, AA
Sergovskaya, NL
Chirskaya, MV
Shorshnev, SV
机构：
[1] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 119991, Russia
[2] ChemBridge Corp, Moscow 119435, Russia
来源：
TETRAHEDRON | 2006年 / 62卷 / 11期
关键词：
azides; boronic acids; cross-coupling; 2,3-dihydrobenzo[b]lfurans; nitriles;
D O I：
10.1016/j.tet.2005.12.026
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Arylboronic acids having a remote azido group were prepared from the corresponding azidosubstituted aryl bromides via lithiation and treatment with trialkyl borates. Preparative yields were achieved when the starting aryl bromides possessed ortho-alkoxy groups, which would stabilize the intermediate aryllithium species. Conventional Suzuki cross-coupling of the arylboronic acids proceeded generally well with retention of azido group; however, sometimes azidomethyl fragment underwent oxidative transformation into a nitrile. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2639 / 2647
页数：9
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