Abstract
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.
Highlights
The design and synthesis of new catalysts is a tedious and time-consuming procedure
Multiple processes performed in an one-reaction vessel, where the product of the first reaction is a substrate for the transformation known as the sequential tandem catalysis, are of great importance for organic chemists.[2,3]
We explored the scope of transvinylation reaction using Grubbs second-generation catalyst (Scheme 1)
Summary
The catalyst can be applied only for a single reaction. One of the major challenges for organic chemists is to develop a multifunctional catalyst that may catalyze more than one reaction in a single vessel. Such a concept is desired from the development of sustainable chemistry to solve the environmental issues.[1] Multiple processes performed in an one-reaction vessel, where the product of the first reaction is a substrate for the transformation known as the sequential tandem catalysis, are of great importance for organic chemists.[2,3] The one-pot approach allows us to simplify the procedure and reduce costs and toxicity by minimizing the purification steps, which is economically and environmentally friendly
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