HCl-Catalyzed Aerobic Oxidation of Alkylarenes to Carbonyls

ChemSusChem. 2022 Jan 21;15(2):e202102326. doi: 10.1002/cssc.202102326. Epub 2021 Dec 9.

Abstract

The construction of C-O bonds through C-H bond functionalization remains fundamentally challenging. Here, a practical chlorine radical-mediated aerobic oxidation of alkylarenes to carbonyls was developed. This protocol employed commercially available HCl as a hydrogen atom transfer (HAT) reagent and air as a sustainable oxidant. In addition, this process exhibited excellent functional group tolerance and a broad substrate scope without the requirement for external metal and oxidants. The mechanistic hypothesis was supported by radical trapping, 18 O labeling, and control experiments.

Keywords: aerobic oxidation; alkylarenes; carbonyls; metal-free; photochemistry.

MeSH terms

  • Catalysis
  • Hydrogen*
  • Indicators and Reagents
  • Oxidants*
  • Oxidation-Reduction

Substances

  • Indicators and Reagents
  • Oxidants
  • Hydrogen