Photochemical Mn-Mediated Generation of Azide Radicals for Improvement of Alkene Hydroxyazidation

Abstract

State-of-the-art strategies for alkene-hydroxyazidation, which yield a mixture of β-azido alcohol and β-azido peroxide, must rely on phosphine reagents to improve the chemoselectivity. To overcome the above problems, we present a photochemical hydroxyazidation of alkenes via Mn-mediated ligand-to-metal charge transfer (LMCT) in O 2, which activates N 3 – to •N 3 and incorporates O 2 to be used as an oxygen source in the hydroxyazidation products. Broad alkene range and step-economy chemistry for the hydroxyazidation transformation were also demonstrated.