Diarylation of Alkenes by a Cu-Catalyzed Migratory Insertion/Cross-Coupling Cascade

A strategy for the catalytic diarylation of alkenes is presented. The method involves the migratory insertion of alkenes into an Ar–Cu complex to generate a new C­(sp3)–Cu complex, which subsequently undergoes reaction with an aryl iodide to constitute a vicinal diarylation of an alkene. The method provides access to benzofuran- and indoline-containing products. Furthermore, highly diastereoselective examples are presented, allowing access to complex, stereochemically rich structures from simple alkene starting materials.