Copper-Catalyzed Synthesis of Masked (Hetero)Aryl Sulfinates

Abstract

Catalysis using substoichiometric copper facilitates the synthesis of masked (hetero)aryl sulfinates under mild, basefree conditions from aryl iodides and the commercial sulfonylation reagent sodium 1-methyl 3-sulfinopropanoate (SMOPS). The development of a tert-butyl ester variant of the SMOPS reagent allowed the use of aryl bromide substrates. The sulfones thus generated can be unmasked and functionalized in situ to form a variety of sulfonyl-containing functional groups.