Tetrabutylammonium Iodide Mediated Synthesis of β-Alkoxy Sulfides and Vinyl Sulfones by Using Benzenesulfonyl Chlorides as the Sulfur Sources under Acidic or Alkaline Conditions

The tetrabutylammonium iodide (TBAI)-promoted generation of sulfur-containing compounds from benzenesulfonyl chlorides and alkenes is described. Under acidic condition, a wide range of -alkoxy sulfides were obtained in good to excellent yields, whereas under alkaline conditions, various vinyl sulfones were produced in moderate to good yields. A novel preparation of (E)--iodovinyl sulfones was achieved through direct difunctionalization of alkynes with benzenesulfonyl chlorides and TBAI.