Fe-Catalyzed oxidative spirocyclization of N-arylpropiolamides with silanes and TBHP involving the formation of C–Si bonds

Abstract

A new iron-catalyzed oxidative spirocyclization of N-arylpropiolamides with silanes and TBHP (tert-butyl hydroperoxide) for the synthesis of 3-silyl spiro[4,5]trienones is presented. The reaction proceeds via a sequence of radical addition, spirocyclization and dearomatization, and offers a practical and straightforward route to introduce silicon-centered radicals into the C–C triple bonds.