Photogenerated Azido Radical Mediated Oxidation: Access to Carbonyl Functionality from Alcohols, Alkylarenes, and Olefins via Organophotoredox

Abstract Azido radical mediated photocatalytic oxidation method for the selective oxidation of various well‐known feedstocks, such as (hetero)aromatic or aliphatic alcohols, alkylarenes, and terminal alkenes, is successfully accomplished. Herein, the catalytic HAT and reversible addition/elimination strategies of azido radical have been explored to convert the commonly oxidizable functionalities into invaluable carbonyls or tertiary alcohols using an organic photocatalyst 4CzIPN with tetrabutyl ammonium azide (TBAN 3 ) and air/O 2 as an oxidant. Indeed, this mild, operationally simple, and productive method offers good to excellent product yields with a wide range of structurally diverse substrates, including pharmaceutical derivatives with good functional group tolerance. Several control experiments have been carried out to investigate the detailed reaction mechanism. magnified image