Enantioselective Construction of C−SCF₃ Stereocenters via Nickel Catalyzed Asymmetric Negishi Coupling Reaction

Abstract

Abstract The construction of the SCF 3 ‐containing 1,1‐diaryl tertiary carbon stereocenters with high enantioselectivities is reported via a nickel‐catalyzed asymmetric C−C coupling strategy. This method demonstrates simple operations, mild conditions and excellent functional group tolerance, with newly designed SCF 3 ‐containing synthon, which can be easily obtained from commercially available benzyl bromide and trifluoromethylthio anion in a two‐step manner. Further substrate exploration indicated that the reaction system could be extended to diverse perfluoroalkyl sulfide (SC 2 F 5 , SC 3 F 7 , SC 4 F 9 , SCF 2 CO 2 Et)‐substituted 1,1‐diaryl compounds with excellent enantioselectivities. The synthetic utility of this transformation was further demonstrated by convenient derivatization to optical SCF 3 ‐containing analogues of bioactive compounds without an apparent decrease in enantioselectivity.