The attachment of per?uoroalkyl groups onto organic compounds has been a major synthetic goal over the past several decades. Previously, our group reported phenanthroline-ligated per?uoroalkyl copper reagents, (phen)CuRF, which react with aryl iodides and aryl boronates to form the corresponding benzo-tri?uorides. Due to the prevalence of heterocycles in pharmaceuticals and agrochemicals, and the greater abundance and lower cost of heteroaryl bromides when compared to that of heteroaryl iodides, the per?uoroalkylation of a series of heteroaryl bromides with (phen)CuCF3 and (phen)CuCF2CF3 has been developed. The mild reaction conditions allow the process to tolerate many common functional groups. Per?uoroethylation with (phen)CuCF2CF3 occurs in somewhat higher yields than tri?uoromethylation with (phen)CuCF3, creating a method to generate ?uoroalkyl heteroarenes that are less accessible from tri?uoroacetic acid derivatives

Copper-mediated per?uoroalkylation of heteroaryl bromides with (phen)CuR<sub>?F</sub>

248th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.

Copper-mediated per?uoroalkylation of heteroaryl bromides with (phen)CuR?F

Copper-mediated per?uoroalkylation of heteroaryl bromides with (phen)CuR_?F