Csp<sup>3</sup>–H Trifluoromethylation of Unactivated Aliphatic Systems
Jiachen He, Truong N. Nguyen, Shuo Guo, Silas P. Cook
Abstract
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.
Topics & Concepts
TrifluoromethylationChemistryReagentAcetonitrileMethyleneAqueous solutionBond cleavageCombinatorial chemistryOrganic chemistryMedicinal chemistryTrifluoromethylCatalysisAlkylFluorine in Organic ChemistryInorganic Fluorides and Related Compounds