A strategy for the synthesis of aryl alpha-ketoamides based upon the acylation of anions derived from cyanomethylamines followed by oxidative cleavage.

[reaction: see text] Cyanomethylamines, prepared by alkylation of amines with chloroacetonitrile, were deprotonated using NaHDMS in THF, reacted with heteroaryl or substitutedphenyl esters, and then oxidized by adding Clorox(TM) to afford aryl alpha-ketoamides in a single operation in good overall yields.