Regio‐ and Stereoselective Vicinal syn‐Arylation‐Trifluoromethylation of Terminal Arylacetylenes

Abstract

AbstractOne‐pot three‐component syn‐arylation‐trifluoromethylation of terminal arylalkynes is developed by using an isolated (phen)Cu(III)(CF3)3 complex (phen: phenanthroline) and aryl boronic acids. This reaction is chemoselective that can suppress the competing trifluoromethylation of alkyne C−H and aryl boronic acids. It is also regioselective to install an aryl group on Cα and a CF3 group on Cβ of arylalkynes. Finally, unusual syn‐difunctionalization chemistry is achieved that is complementary to the general anti‐stereochemistry for difunctionalization of alkynes involving trifluoromethylation. The use of a Cu(III)−CF3 complex is crucial to the success that not only acts as a reactive CF3 precursor, but is also responsible for the unusual syn‐stereochemistry. This study allows ready access to vicinal arylated‐trifluoromethylated olefins, which is a widely existing structural motif in many biologically active compounds.