Visible-Light-Induced Stoichiometric Coupling of Alkylarenes and Trifluoromethyl Ketones

A visible-light induced direct C-(sp(3))-H functionalizationof alkylarenes with trifluoromethyl ketones has been reported to accessvaluable benzyl-substituted trifluoromethyl alcohols in a stoichiometricmanner. Readily available petroleum-derived alkylarenes are employedas latent benzylation reagents. With a bromine radical as the hydrogenatom transfer reagent, primary, secondary, and tertiary benzyl C-Hbonds are suitable coupling partners. Additionally, the late-stagemodification of bioactive molecules highlights the potential applicationof this approach.

Automated summary

This study reports a visible-light induced C-(sp(3))-H functionalization of alkylarenes with trifluoromethyl ketones, enabling the synthesis of valuable benzyl-substituted trifluoromethyl alcohols in a stoichiometric manner. Petroleum-derived alkylarenes are used as latent benzylation reagents. Bromine radical serves as the hydrogen atom transfer reagent, allowing for coupling of primary, secondary, and tertiary benzyl C-H bonds. The late-stage modification of bioactive molecules highlights the potential application of this approach.