Cobalt–Tertiary-Amine-Mediated Hydroxytrifluoromethylation of Alkenes with CF₃Br and Atmospheric Oxygen

Abstract

The mild and efficient hydroxytrifluoromethylation of alkenes with bromotrifluoromethane (CF3Br) and atmospheric oxygen mediated by cobalt-tertiary amine is described. This reaction proceeds with broad substrate scope and good functional group compatibility. Mechanistic studies indicate that the reaction proceeds through a radical pathway, which is enabled by combination of the previously unexplored highly efficient N-isopropyl-N,2-dimethylpropan-2-amine with Co(II) for the single electron reduction of CF3Br to CF3 radical.