Synthesis of quaternary centres by single electron reduction and alkylation of alkylsulfones

Abstract

A new method for the generation of tertiary radicals through single electron reduction of alkylsulfones promoted by Zn and 1,10-phenanthroline has been developed. These radicals could be employed in the Giese reaction, affording structurally diverse quaternary products in good yields. With the high modularity and functional group compatibility of sulfones, the utility of this method was demonstrated by intramolecular and iterative reactions to give complex structures. The radical generation process was investigated by control experiments and theoretical calculations.