Acid-catalyzed regioselective remote heteroarylation of alkenes via CC bond migration

Abstract

We report herein the acid-catalyzed regioselective remote heteroarylation and reductive alkylation of alkenes. Various alkenes, including mono-, di-, and tri-substituted alkenes and cyclic alkenes, are applicable to this reaction. This method exhibits broad substrate scope, high functional group tolerance and high atomic economy. In addition, both gram-scale synthesis and product transformations demonstrate the potential utility of this reaction. It also provides an efficient and novel pathway to establish the valuable framework of 1,1-diaryl alkanes. Further mechanistic studies suggested that TfOH in situ generated by Cu(OTf)₂ and trace H₂O catalyzed the alkene migration. Then, heteroarylation was conducted by Friedel–Crafts type alkylation.