The visible light catalyzed methylsulfoxidation of (het)aryl diazonium salts using DMSO is illustrated. This is the first example of DMSO being used as the source of the methylsulfinyl group. The procedure tolerates a wide range of functional groups on (het)aryl diazonium salts and provides aryl methyl sulfoxides in excellent yields under mild reaction conditions.
A visible-light-driven
photoredox-catalyzed multicomponent reaction
of 2-vinylanilines, sulfonyl chlorides, and sulfur ylides is described.
This protocol features redox-neutral mild conditions, a broad substrate
scope, and good functional group tolerance, providing access to various
sulfonated 2,3-disubstituted indolines. The product can be transformed
to a diverse range of functionalized indoles by a selective aromatization/nucleophilic
substitution process. Mechanistic investigations suggest that both
sulfonyl chlorides and sulfur ylides serve as radical sources, and
the reaction proceeds through a sequential radical addition/addition/thermal
SN2-substitution process.
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