Synthesis of Diaryl Thiosulfonates via Electrochemical Cascade S─S‐Coupling Using Arylsulfonyl Chlorides/Arylsulfinate Salts

Single component does double duty! Arylsulfinate salts or arylsulfonyl chlorides alone act as the source of both the arylsulfonyl and arylsulfide fragments via electrochemical autocatalytic processes to generate diarylthiosulfonate. Wide substrate scope was demonstarted with minimum waste generation.

Abstract

A facile and straightforward electrochemical method for synthesizing diaryl thiosulfonates is reported. The process involves a combination of consecutive in situ electrochemical–autocatalytic processes, followed by a C─S coupling sequence, to enable the formation of diaryl thiosulfonates using either arylsulfinate salts or arylsulfonyl chlorides alone. Thus, unlike previous methods, it avoids using stoichiometric thiol or disulfide reaction partners, over-stoichiometric promoters, metal-based redox reagents, or catalysts, thereby minimizing the formation of undesired products and chemical waste. A range of arylsulfinate salts/arylsulfonyl chlorides was screened under the reaction conditions, yielding the corresponding diaryl thiosulfonates in moderate-to-good yields.

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