Copper-Mediated Fluoroalkylation of Aryl Bromides and Chlorides Enabled by Directing Groups

This report describes the reactions between N heterocyclic carbene copper(I) fluoroalkyl complexes and aryl halides bearing ortho-directing groups. Pyridine, pyrazole, oxazoline, imine, and ester directing groups are shown to dramatically enhance the reactivity of aryl bromides and chlorides with (IPr)CuI-fluoroalkyl complexes (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene; fluoroalkyl = difluoromethyl and pentafluoroethyl) to afford aryl-fluoroalkyl coupling products. This approach is leveraged to achieve the Cu-catalyzed directed fluoroalkylation of a series of aryl bromide substrates.

Automated summary

This report describes the Cu-catalyzed directed fluoroalkylation of aryl bromide substrates using N heterocyclic carbene copper(I) fluoroalkyl complexes and aryl halides bearing ortho-directing groups such as pyridine, pyrazole, oxazoline, imine, and ester. These directing groups significantly enhance the reactivity of aryl bromides and chlorides with (IPr)CuI-fluoroalkyl complexes, leading to the formation of aryl-fluoroalkyl coupling products.