Chemo- and Enantioselective Oxidative α-Azidation of Carbonyl Compounds.

We report high-performance I /H O catalysis for the oxidative or decarboxylative oxidative α-azidation of carbonyl compounds by using sodium azide under biphasic neutral phase-transfer conditions. To induce higher reactivity especially for the α-azidation of 1,3-dicarbonyl compounds, we designed a structurally compact isoindoline-derived quaternary ammonium iodide catalyst bearing electron-withdrawing groups. The nonproductive decomposition pathways of I /H O catalysis could be suppressed by the use of a catalytic amount of a radical-trapping agent.