Friedel–Crafts alkylation between chalcone epoxides and heteroarenes induced by triarylaminium salt

Abstract

Triarylaminium salt was disclosed as a highly efficient nonmetallic initiator for the Friedel–Crafts reaction between chalcone epoxides and heteroarenes to construct a series of complex β-heteroaryl α-ketols in mild conditions and with good yields. Chalcone epoxides were presented as valuable halogen-free pre-electrophile in Friedel–Crafts alkylation through the formation of the stabilized benzylic cation intermediates. A plausible radical cation chain mechanism was also proposed.