Direct Oxygenation of C-H Bonds through Photoredox and Palladium Catalysis

J Org Chem. 2020 Mar 6;85(5):3426-3439. doi: 10.1021/acs.joc.9b03197. Epub 2020 Jan 28.

Abstract

This report presents the oxygenation of C-H bonds via the merger of photocatalysis and Pd catalysis. Herein, we describe the utilization of a photocatalyst to oxidize an organopalladium(II) intermediate to high-valent PdIII or PdIV intermediates, which promotes the formation of C-O bonds. The demonstrated method works efficiently with various directing groups, such as oxime ether and benzothiazole. The applicability of this direct C-O bond formation method is shown by synthesizing several metal complexes of 2-(benzo[d]thiazol-2-yl)phenol that can be used in organic light-emitting diodes and pharmaceuticals.

Publication types

  • Research Support, Non-U.S. Gov't