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

Abstract

AbstractThe construction of the SCF3‐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 SCF3‐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 (SC2F5, SC3F7, SC4F9, SCF2CO2Et)‐substituted 1,1‐diaryl compounds with excellent enantioselectivities. The synthetic utility of this transformation was further demonstrated by convenient derivatization to optical SCF3‐containing analogues of bioactive compounds without an apparent decrease in enantioselectivity.