Copper-catalyzed three-component reaction of arylhydrazine hydrochloride, DABSO, and NFSI for the synthesis of arenesulfonyl fluorides

Qijun Pan; Yongan Liu; Wan Pang; Jingjing Wu; Xiaoyu Ma; Xiaojun Hu; Yong Guo; Qing-Yun Chen; Chao Liu

doi:10.1039/d1ob01697k

Copper-catalyzed three-component reaction of arylhydrazine hydrochloride, DABSO, and NFSI for the synthesis of arenesulfonyl fluorides

Org Biomol Chem. 2021 Oct 27;19(41):8999-9003. doi: 10.1039/d1ob01697k.

Authors

Qijun Pan¹, Yongan Liu², Wan Pang¹, Jingjing Wu¹, Xiaoyu Ma¹, Xiaojun Hu¹, Yong Guo², Qing-Yun Chen², Chao Liu^{1

2}

Affiliations

¹ School of Chemical and Environmental Engineering, Shanghai Institute of Technology, 100 Haiquan Road, Shanghai 201418, China. maxiaoyu@sit.edu.cn.
² Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

PMID: 34605502
DOI: 10.1039/d1ob01697k

Abstract

This paper reports a convenient copper-catalyzed three-component conversion of arylhydrazine hydrochlorides to arenesulfonyl fluorides in good yields under mild conditions, using 1,4-diazabicyclo [2.2.2]octane bis(sulfur dioxide) (DABSO) as a sulfonyl source and N-fluorobenzenesulfonimide (NFSI) as a fluorine source based on a radical sulfur dioxide insertion and fluorination strategy. Notably, arylhydrazine hydrochloride is used as a safe precursor of aryl radicals.

Publication types

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