Base-Promoted Ring-Opening Hydroxylation of Cyclic Sulfonium Salts

Abstract

Herein, we reported a general strategy for the synthesis of sulfur-containing primary alcohol derivatives by base-promoted ringopening hydroxylation of cyclic sulfonium salts. A variety of sulfonium salts were successfully transformed into the desired hydroxylated products in moderate to excellent yields with good functional group tolerance. Moreover, the one-pot synthesis, scale-up reaction, and late-stage functionalization of complex molecules demonstrated the practicability of this synthetic protocol in the field of synthetic chemistry.

Synthesis of alkynyl sulfides via base-promoted nucleophilic ring-opening of α-bromostyrene sulfonium salt

“…12 In our pursuit of developing a novel and efficient method for synthesizing alkynyl sulfides, we directed our attention towards cyclic sulfonium salts since they had shown promising results in the formation of organic sulfides. 13 Herein, we report a practical and efficient strategy for the formation of alkynyl sulfides using tetramethylene sulfoxide as the sulfur source via an α-bromostyrene sulfonium salt. The reaction proceeds with good functional group tolerance and could also be applied to the late-stage functionalization of bioactive molecules and drugs (Scheme 1e).…”