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自由基促进的芳基 C-H 硅烷化反应。

Free-Radical-Promoted Site-Selective C-H Silylation of Arenes by Using Hydrosilanes.

机构信息

State Key Laboratory of Applied Organic Chemistry, Lanzhou University , Lanzhou 730000, China.

State Key Laboratory Cultivation Base for TCM Quality and Efficacy, College of Pharmacy, Nanjing University of Chinese Medicine , Nanjing 210023, China.

出版信息

Org Lett. 2017 Oct 20;19(20):5573-5576. doi: 10.1021/acs.orglett.7b02717. Epub 2017 Sep 29.

Abstract

A free-radical-promoted aryl/heteroaryl C-H silylation using hydrosilane was developed. This cross-dehydrogenative silylation enables both electron-rich and electron-poor aromatics to afford the desired arylsilanes in unique selectivity. A "para-selectivity" was observed by examination of over 54 examples. This exceptional orientation is quite different from that in Friedel-Crafts C-H silylation or transition-metal-catalyzed dehydrogenative silylation.

摘要

发展了一种自由基促进的芳基/杂芳基与硅烷的 C-H 硅烷化反应。这种交叉脱氢硅烷化反应可以使富电子和缺电子的芳基化合物以独特的选择性得到所需的芳基硅烷。通过对超过 54 个例子的考察,观察到了“对位选择性”。这种特殊的取向与傅-克 C-H 硅烷化或过渡金属催化的脱氢硅烷化反应完全不同。

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