Organomediated electrochemical fluorosulfonylation of aryl triflates via selective C–O bond cleavage

Xianqiang Kong (), Yiyi Chen, Xiaohui Chen, Cheng Ma, Ming Chen, Wei Wang, Yuan-Qing Xu, Shao-Fei Ni () and Zhong-Yan Cao ()
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Xianqiang Kong: Changzhou Institute of Technology
Yiyi Chen: Changzhou Institute of Technology
Xiaohui Chen: Changzhou Institute of Technology
Cheng Ma: Shantou University
Ming Chen: Changzhou University
Wei Wang: Changzhou Institute of Technology
Yuan-Qing Xu: Henan University
Shao-Fei Ni: Shantou University
Zhong-Yan Cao: Henan University

Nature Communications, 2023, vol. 14, issue 1, 1-8

Abstract: Abstract Although aryl triflates are essential building blocks in organic synthesis, the applications as aryl radical precursors are limited. Herein, we report an organomediated electrochemical strategy for the generation of aryl radicals from aryl triflates, providing a useful method for the synthesis of aryl sulfonyl fluorides from feedstock phenol derivatives under very mild conditions. Mechanistic studies indicate that key to success is to use catalytic amounts of 9, 10-dicyanoanthracene as an organic mediator, enabling to selectively active aryl triflates to form aryl radicals via orbital-symmetry-matching electron transfer, realizing the anticipated C–O bond cleavage by overcoming the competitive S–O bond cleavage. The transition-metal-catalyst-free protocol shows good functional group tolerance, and may overcome the shortages of known methods for aryl sulfonyl fluoride synthesis. Furthermore, this method has been used for the modification and formal synthesis of bioactive molecules or tetraphenylethylene (TPE) derivative with improved quantum yield of fluorescence.

Date: 2023
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DOI: 10.1038/s41467-023-42699-0

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