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Electrophilic Chlorine from Chlorosulfonium Salts: A Highly Chemoselective Reduction of Sulfoxides.

Herein, we describe a selective late-stage deoxygenation of sulfoxides based on a novel application of chlorosulfonium salts and, a new process using them generated in situ from sulfoxides as the source of electrophilic chlorine. The use of highly nucleophilic 1,3,5-trimethoxybenzene (TMB) as the reducing agent is described for the first time and applied successfully in the deoxygenation of simple and functionalized sulfoxides. The method is easy to handle, economic, appropriate for gram scale and decidedly appropriate for poly-functionalized molecules, as demonstrated with more than 45 examples, including commercial medicines and analogues. We also report some competition experiments to define the more reactive sulfoxide and a mechanistic proposal based on substrate and product observations.