Facile Synthesis of Diaryl Sulfones through Arylsulfonylation of Arynes and Thiosulfonates

Abstract

A mild and transition-metal-free arylsulfonylation reaction of arynes has been developed. Arynes generated in situ from 2-(trimethylsilyl)aryl triflates undergo nucleophilic addition with thiosulfonates to produce diaryl sulfones in 41–99% yield. The reaction can be scaled easily to gram-scale with the high yield maintained. Finally, mechanistic experiments showed that acetonitrile acted as a proton source.

Key words

arynes - thiosulfones - aryl sulfones - coupling - aryl–sulfur bonds

Publication History

Received: 11 August 2022

Accepted after revision: 26 December 2022

Accepted Manuscript online:
26 December 2022

Article published online:
13 January 2023

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