Nickel-Catalyzed Cross-Coupling of Acyl Chloride with Racemic alpha-Trifluoromethyl Bromide to Access Chiral alpha-Trifluoromethyl Ketones

The nickel-catalyzed reductive cross-coupling reaction of acyl chloride with racemic secondary alpha-trifluoromethyl bromide has been developed. By this chemistry, a series of structurally interesting chiral alpha-CF3 carbonyl compounds could be accessed with great enantioselectivity and good functional group tolerance. The study of late-stage transformation indicated that this chemistry could be used as the robust method to prepare products that contain a bioactive motif. Furthermore, the importance of the alpha-trifluoromethyl group to this reaction has been illustrated by control experiments.