Abstract
Density functional theory (DFT) calculations were employed to study the mechanism for copper-catalyzed trifluoromethylation of aryl boronic acids by Togni’s reagent. Computational results suggest that the catalytic cycle proceeds with the transmetallation between phenylboronic acid and copper(I) species, which generates a phenylcopper(I) intermediate. Subsequent coordination of Togni’s reagent and the electrophilic substitution of CF3 group to phenyl group finally afford the trifluoromethylation product through a concerted five-membered ring transition state. The transmetallation process with an activation free energy of 21.7 kcal/mol is determined to be the rate-determining step of this reaction. Moreover, the reactivity of alkylboronic acid was also calculated and proven to be unfavorable due to the higher activation free energy of transmetallation process.
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