Cobalt–Tertiary-Amine-Mediated Hydroxytrifluoromethylation of Alkenes with CF<sub>3</sub>Br and Atmospheric Oxygen
Qiankun Li, Fan Wu, Deqian Peng, Bingyin Meng, Shaohan Wang, Rui Huang, Shihao Liu, Suhua Li
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.
Topics & Concepts
CobaltAmine gas treatingChemistryIsopropylCatalysisOxygenRadicalTertiary amineFunctional groupPhotochemistryCombinatorial chemistryOrganic chemistryPolymerFluorine in Organic ChemistryInorganic Fluorides and Related CompoundsPer- and polyfluoroalkyl substances research