Enantioselective preparation of atropisomeric biaryl trifluoromethylsulfanes via ring-opening of cyclic diaryliodoniums

Abstract

Two convenient and practical methods for the synthesis of axially chiral biaryls bearing the trifluoromethylthio group are reported. A Cu-catalyzed enantioselective ring-opening reaction of cyclic diaryliodoniums with CsSCF₃ enables the direct synthesis of trifluoromethylthiolated biaryl atropisomers in high yields and enantioselectivity. For unsymmetric cyclic diaryliodoniums bearing an adjacent group to the C–I bond, a two-step procedure is required to achieve good regio- and enantioselectivity.