Photochemical Selective Oxidation of Benzyl Alcohols to Aldehydes or Ketones

J Org Chem. 2023 Apr 7;88(7):4765-4769. doi: 10.1021/acs.joc.2c02667. Epub 2023 Mar 29.

Abstract

Using Eosin Y as a metal-free photocatalyst and O2 as an oxidant, the present study reports a new photochemical protocol that enables efficient aerobic oxidation of various benzyl alcohols to the corresponding aldehydes or ketones in excellent yields under mild reaction conditions. The catalyst system presents good functional-group tolerance and exquisite chemoselectivity, which also can easily be scaled-up to gram scale. Moreover, the methodological applications in practical synthesis of several organic molecules and the primary reaction mechanism were also discussed.