Csp3-H Trifluoromethylation of Unactivated Aliphatic Systems

A straightforward method for the undirected trifluoromethylation of unactivated methylene units was developed. The reaction proceeds in aqueous acetonitrile with Grushin's reagent, bpyCu(CF3)(3), under broad-spectrum white-light irradiation. The trifluoromethylation tolerates a wide range of functional groups including ketones, esters, nitriles, amides, alcohols, and carboxylic acids. The C-H cleavage step is performed via intermolecular H atom abstraction, and the selectivities across a range of methylene units are reported. Mechanistic studies offer a general reaction coordinate for the overall transformation.

Automated summary

A method for trifluoromethylation of unactivated methylene units has been developed, tolerating a wide range of functional groups, with mechanistic studies providing a general reaction coordinate for the overall transformation.