Mechanochemically Triggered Deaminative Alkylation of Heterocycles Using Katritzky’s Salts

Herein, we describe a mechanochemical-assisted C-H alkylation of quinoxalinones and quinoline-<i>N</i>-oxides with Katritzky's salts. These salts are excellent alkyl precursors synthesized from alkyl amines. Our key finding is that these salts with moderate C-N bond dissociation energy generate alkyl radicals under mechanochemical stress. Mechanistic insights reveal that mechanical stress facilitates the homolytic scission of the C-N bond of Katritzky's salts, leading to the formation of an alkyl radical intermediate.