Mild Synthesis of Sulfonium Salts from Hypervalent Iodine Benzyne Precursors

Abstract

Interest in efficient protocols for obtaining sulfonium salts are stemmedfrom their tremendous applications. Arylsulfonium salts are highly photosensitive and are well known for their ability of releasing protons under UV conditions. Thus, they are widely used as photoinitiators applied in the fields of coatings and materials. From the synthetic standpoint, they can serve as aryl or alkyl donation sources, forming interesting organic frameworks. Therefore, access to these compounds is highly desired. Recently, our group reported an efficient benzyne precursor, pseudocyclic arylbenziodoxaboroles, that can be generated in mild conditions: treatment with water or weak base at room temperature. Reactions of such benzyne precursor with various sulfide substrates allow for diverse functionalized sulfonium salts obtained in moderate to excellent yield.