Accessing Medium-Sized Rings via Vinyl Carbocation Intermediates

Abstract

Medium-sized rings (8-11-membered cycles) are often more challenging to synthesize than smaller rings (5-7-membered cycles) due to ring strain. Herein, we report a catalytic method for forming 8- and 9-membered rings that proceeds via the intramolecular Friedel-Crafts reactions of vinyl carbocation intermediates. These reactive species are generated catalytically through the ionization of vinyl toluenesulfonates by a Lewis acidic lithium cation-weakly coordinating anion salt.