TBAI-catalyzed oxidative synthesis of benzamides from acetophenones and carbinols

Org Biomol Chem. 2014 Sep 7;12(33):6359-62. doi: 10.1039/c4ob01203h.

Abstract

An interesting and convenient procedure for the oxidative transformation of acetophenones and carbinols to primary benzamides has been developed. By using tetra-n-butylammonium iodide (TBAI) as the catalyst and tert-butyl hydroperoxide (TBHP) as the oxidant, the desired benzamides were isolated in moderate to good yields in aqueous solution. Notably, not only acetophenones but also propiophenones can be applied as substrates as well. Hence, we believe that this new procedure is not just a catalytic version of the iodine-based method.