HFIP-Assisted Single C-F Bond Activation of Trifluoromethyl Ketones using Visible-Light Photoredox Catalysis

A visible light photoredox catalytic method for the selective cleavage of single strong C-F bond in trifluoromethyl ketones is reported. Single electron reduction of trifluoromethyl ketones generates difluoromethyl radicals which can be engaged in intermolecular C-C bond formation with N-methyl-N-arylmethacrylamides to furnish fluorine-containing oxindole derivatives in good yields. The reaction shows excellent chemoselectivity with good functional group tolerance under mild conditions. 1,1,1,3,3,3-Hexafluoroisopropanol (HFIP) as a solvent plays a critical role for the selective single C-F bond cleavage. High-level DFT calculations are depicted to shed light on the mechanism.

Automated summary

This study presents a novel visible light photoredox catalytic method for the selective cleavage of a single strong C-F bond in trifluoromethyl ketones. The reaction shows excellent chemoselectivity and functional group tolerance under mild conditions, and high-level DFT calculations are used to elucidate the mechanism.