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

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 Pd-III or Pd-IV 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.