Dimethylamino-iodine(iii)/PPh3-mediated synthesis of α-ketoamides from glyoxylic acids

Abstract

The development of efficient synthetic approaches to α-ketoamides remains a significant objective. Herein, we report a mild and metal-free method for the preparation of α-ketoamides from glyoxylic acids, mediated by a dimethylamino-iodine(III)/PPh₃ system. This method is further utilized for the in situ generation of amino-based hypervalent iodine(III) reagents, which enable the formation of diverse α-ketoamides. Mechanistic studies suggest that the transformation proceeds through an ionic pathway, involving the formation of an active dimethylamino-phosphonium species derived from the reaction between the novel dimethylamino-iodine(III) reagent (DMI) and PPh₃.