Brønsted base catalyzed Reppe sulfonylation reaction

Abstract

Reppe carbonylation is well-studied and extensively employed in industry, while the exploration and development of the Reppe sulfonylation reaction are still in their infancy. In this research, we have introduced a novel method for Reppe sulfonylation, which incorporates sulfur dioxide without the need for metal catalysts, utilizing Brønsted bases instead. This technique presents a promising and efficient pathway for the synthesis of sulfonates, which possess wide-ranging applications. Our method facilitates the direct transformation of a vast spectrum of readily available alcohols (exceeding 70 variants) into their corresponding sulfonates, with yields varying from moderate to excellent. Furthermore, our approach is compatible with primary and secondary alkanols, and diols, efficiently yielding Reppe sulfonylation products. Significantly, this methodology is amenable for the late-stage functionalization of complex molecules, supporting a broad array of functional groups.