<i>N</i>-Alkynylthio Phthalimide: A Shelf-Stable Alkynylthio Transfer Reagent for the Synthesis of Alkynyl Thioethers

Abstract

A new kind of electrophilic alkynylthiolating reagent, called <i>N</i>-alkynylthio phthalimide, is designed and synthesized herein. This electrophilic sulfenylating reagent can be easily prepared in three steps from commercially available phthalimide and corresponding silver acetylide. Furthermore, the <i>N</i>-alkynylthio phthalimides are demonstrated to be efficient alkynylthio transfer reagents that can react with various C-nucleophiles, including β-ketoesters, aryl boronic acids, and Grignard reagents to afford a diverse range of alkynyl thioethers under mild conditions.