Dual Activity of Grubbs-Type Catalyst in the Transvinylation of Carboxylic Acids and Ring-Closing Metathesis Reactions.

The development of a multifunctional catalyst, which mimics the promiscuity of enzymes, that would catalyze more than one chemical transformation in a single reaction vessel is one of the key points of modern sustainable chemistry. The results of our experiments indicated that Grubbs-type catalysts possess such multitask activity, catalyzing the transvinylation reaction of carboxylic acids without losing their original metathetic activity. This new activity of Grubbs catalysts was evidenced on several examples. It allows us to design a transvinylation/ring-closing metathesis (RCM) cascade reaction leading to the formation of endocyclic enol lactones from unsaturated carboxylic acids in an one-pot procedure. This unique ability of Grubbs catalyst to catalyze multiple mechanically distinct cascade reactions in a chemoselective way offers the new possibility for the synthesis of complex compounds from simple, easily accessible substrates.