Mechanistic Study of Copper-Catalyzed C-H Hydroxylation/C-S Coupling by ESI-HR MS and DFT Calculations

Molecules. 2017 Nov 6;22(11):1912. doi: 10.3390/molecules22111912.

Abstract

The reaction mechanism of Cu-catalyzed C-H hydroxylation/C-S coupling was studied using electrospray ionization high resolution mass spectrometry (ESI-HR MS) and density functional theory calculations (DFT). Notably, a series of CuI and CuIII complexes were observed as key intermediates and identified using ESI-HR MS. Furthermore, a catalyst cycle involving proton abstraction/oxidative addition/reductive elimination was proposed. This study is important and valuable with respect to C-H functionalization.

Keywords: C-H hydroxylation/C-S coupling; Cu-catalyzed; DFT; ESI-HR MS; reaction mechanism.

MeSH terms

  • Catalysis
  • Copper / chemistry*
  • Hydroxylation
  • Models, Molecular
  • Molecular Structure
  • Spectrometry, Mass, Electrospray Ionization / methods*

Substances

  • Copper