Decarboxylative sulfation by persulfates

Abstract

Direct decarboxylative sulfation via C–O bond formation is an unexplored disconnection strategy for the synthesis of organosulfates, with the potential to overcome the significant limitations of O-sulfonation, which is restricted to hydroxyl-containing compounds. Reported here is a radical process for direct decarboxylative sulfation by persulfates. In this reaction, persulfates serve a dual role: acting as a versatile oxidant to generate carbon-centered radicals in decarboxylation, and providing an O–O source to facilitate the synthesis of organosulfates via C–OSO₃⁻ bond formation. This method enables the replacement of diverse carboxylic acids with ionizable organosulfate groups, which could be potential isosteres to improve molecules’ metabolic profiles.