Electroreductive Desulfurative Transformations with Thioethers as Alkyl Radical Precursors

17 March 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


Herein, the use of aryl alkyl thioethers as precursors for C-centered alkyl radicals is demonstrated for desulfurative C-H and C-C bond formation under electroreductive conditions. The transformations occur with complete selectivity for C(sp3)-S bond cleavage, orthogonal to that of transition metal-catalyzed two-electron routes. Experimental and theoretical studies provide mechanistic insights that serve as a steppingstone for future use of thioethers as efficient radical precursors that can outcompete their established sulfone analogues.


Giese reaction
C-S bond cleavage
radical chemistry
organic synthesis
alkyl radical
radical-polar crossover


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