Copper-Mediated Perfluoroalkylation of Heteroaryl Bromides with (phen)CuRF

The attachment of perfluoroalkyl groups onto organic compounds has been a major synthetic goal over the past several decades. Previously, our group reported phenanthroline-ligated perfluoroalkyl copper reagents, (phen)CuR_F, which react with aryl iodides and aryl boronates to form the corresponding benzotrifluorides. Herein the perfluoroalkylation of a series of heteroaryl bromides with (phen)CuCF₃ and (phen)CuCF₂CF₃ is reported. The mild reaction conditions allow the process to tolerate many common functional groups. Perfluoroethylation with (phen)CuCF₂CF₃ occurs in somewhat higher yields than trifluoromethylation with (phen)CuCF₃, creating a method to generate fluoroalkyl heteroarenes that are less accessible from trifluoroacetic acid derivatives. Read more on publisher's site.