Sulfonylation of Benzylic C-H Bonds through the Reaction of Aryl(o-tolyl)methanones with Sulfonyl Hydrazides or Sulfonyl Chlorides

Xinxing Gong; Jiahao Chen; Xiaofang Li; Wenlin Xie; Jie Wu

doi:10.1002/asia.201800591

Sulfonylation of Benzylic C-H Bonds through the Reaction of Aryl(o-tolyl)methanones with Sulfonyl Hydrazides or Sulfonyl Chlorides

Chem Asian J. 2018 Sep 4;13(17):2543-2548. doi: 10.1002/asia.201800591. Epub 2018 Jul 12.

Authors

Xinxing Gong¹, Jiahao Chen¹, Xiaofang Li², Wenlin Xie², Jie Wu^{1

3}

Affiliations

¹ Department of Chemistry, Fudan University, 2005 Songhu Road, Shanghai, 200438, P. R. China.
² School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, 411201, P. R. China.
³ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. China.

PMID: 29791085
DOI: 10.1002/asia.201800591

Abstract

A sulfonylation of benzylic C-H bonds of aryl(o-tolyl)methanones with arylsulfonyl hydrazides or arylsulfonyl chlorides has been developed. Arylsulfonyl hydrazides and arylsulfonyl chlorides were employed as sulfonylating reagents respectively to complete this transformation. During the reaction, enols were generated in situ from aryl(o-tolyl)methanones under UV irradiation, and subsequently reacted with sulfonyl radicals to provide a range of aryl(2-(arylsulfonylmethyl)aryl)methanones.

Keywords: UV irradiation; radical reactions; reaction mechanisms; sulfonylation; synthetic methods.

Abstract

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