C-H bond functionalizations with palladium(II): intramolecular oxidative annulations of arenes

被引:119
作者
Ferreira, Eric M. [1 ]
Zhang, Haiming [1 ]
Stoltz, Brian M. [1 ]
机构
[1] CALTECH, Arnold & Mabel Beckman Labs Chem Synth, Div Chem & Chem Engn, Pasadena, CA 91125 USA
关键词
D O I
10.1016/j.tet.2008.01.052
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Oxidative annulations for the synthesis of carbocycles were developed using a catalytic palladium(II) system. Indoles with pendant olefin tethers were oxidatively cyclized to form annulated products. Electron-rich aromatic systems were also investigated, culminating in the synthesis of benzofurans and dihydrobenzofurans by a similar protocol. These reactions were demonstrated to proceed by an initial C-H bond functionalization event, followed by olefin insertion and beta-hydride elimination. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5987 / 6001
页数:15
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