Friedel–Crafts reactions catalyzed by samarium diiodide

Abstract

Samarium diiodide is an efficient precatalyst for the Friedel–Crafts reaction involving various aromatic substrates and chelating electrophiles. Alkyl 3,3,3-trifluoropyruvates are transformed into α-hydroxyesters in good yields with total regioselectivity. In reactions involving an ethyl glyoxylate or a glyoxylic imine, α-hydroxyesters or α-aminoesters are obtained with variable amounts of products resulting from a double Friedel–Crafts reaction.