Stereoselective Synthesis of Alkenyl Fluorides and Alkynes by Defluoro Coupling of Trifluoromethyl Arenes

Abstract A practical method for the stereoselective synthesis of tri‐ and tetra‐substituted 1,2‐fluoro‐borylalkenes and alkynes by defluoro / C–C coupling of aryl trifluoromethyl groups is disclosed. Transformations convert simple abundant CF 3 –arenes and multifunctional organodiboron reagents in the presence of a Lewis base activator into coupled products in up to 94% yield and >98:2 Z/E selectivity. Synthetic utility is highlighted by several product transformations that access an array of diverse scaffolds.