Sulfinylation of Tertiary Alkyl Halides via a Halogenophilic Substitution (SN2X) Reaction

Abstract

The halogenophilic S_N2X reaction involving a nucleophilic attack on the X group from the front is less sensitive to backside steric hindrance. Herein, we report a mild and efficient S_N2X reaction for sulfinylation of activated tertiary alkyl halides, which could provide a novel method for accessing sulfoxides decorated with a congested carbon center. Preliminary mechanistic studies indicated that the generated sulfinyl bromides would be the key electrophilic intermediates in the reaction.