Abstract

Divergent synthesis of α-C–H methylated pyrazines and pyrazinones using dimethyl sulfoxide as a nonconventional methylating agent under metal-free conditions was reported. Dimethyl sulfoxide-coordinated bromine cation pools generated from the treatment of dimethyl sulfoxide and 1,2-dibromoethane undergo Pummerer-type fragmentation to afford an electrophilic methyl(methylene)sulfonium ion for reaction with a carbon nucleophile followed by aromatization to afford α-methylated pyrazines and pyrazinones.