Substrate- and temperature-controlled divergence in reactions of alcohols with TosMIC catalyzed by BF3 center dot Et2O: Facile access to sulfinates and sulfones

摘要

An efficient BF3Et2O-catalyzed divergent synthesis of sulfinate esters and sulfones through C-O and C-S bond formation has been achieved from alcohols and p-toluenesulfonylmethyl isocyanide (TosMIC). Various alcohols reacted smoothly with TosMIC under the present conditions at room temperature providing sulfinate esters exclusively. By tuning the reaction temperature, the alcohols that provide highly stabilized carbocation in the reaction medium afforded sulfones as sole products. This study was aimed at understanding the regioselectivity of ambidentate sulfinate ion and to elucidate the interpretation of sulfinate/sulfone scaffolds.