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

Zhengbao Xu; Li Chai; Zhong-Quan Liu

doi:10.1021/acs.orglett.7b02717

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

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

Authors

Zhengbao Xu¹, Li Chai¹, Zhong-Quan Liu^{1

2}

Affiliations

¹ State Key Laboratory of Applied Organic Chemistry, Lanzhou University , Lanzhou 730000, China.
² State Key Laboratory Cultivation Base for TCM Quality and Efficacy, College of Pharmacy, Nanjing University of Chinese Medicine , Nanjing 210023, China.

PMID: 28961005
DOI: 10.1021/acs.orglett.7b02717

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.

Publication types

Research Support, Non-U.S. Gov't