Nickel-Catalyzed Cross-Coupling of Acyl Chloride with Racemic α-Trifluoromethyl Bromide to Access Chiral α-Trifluoromethyl Ketones
Juanjuan Wu, Hongli Wu, Xinyu Liu, Yuekun Zhang, Genping Huang, Chun Zhang
Abstract
The nickel-catalyzed reductive cross-coupling reaction of acyl chloride with racemic secondary α-trifluoromethyl bromide has been developed. By this chemistry, a series of structurally interesting chiral α-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 α-trifluoromethyl group to this reaction has been illustrated by control experiments.
Topics & Concepts
TrifluoromethylChemistryBromideCatalysisChlorideNickelCoupling reactionOrganic chemistryCombinatorial chemistryMedicinal chemistryAlkylFluorine in Organic ChemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods