Imidazole Backbone Functionalization with Olefin Cross-Metathesis

Abstract

A selective and high-rate Ru-catalyzed cross-metathesis reaction of alkenes with vinylimidazole is disclosed. Cross-metathesis is known to operate less efficiently on N-heterocycles, but through optimization by means of statistical experimental design and multiple regression, optimal reaction conditions were identified that allowed for consistent high-yields without the need of overly complicated set-ups or additives. The method was tested on a series of terminal alkene reagents with a variety of different functional groups and it provides the corresponding target molecules in good to high yields.