Development of Combo Metal Catalysis for Rapid 1,3-Rearrangement of Propargyl Alcohols and Its Application to Efficient Transformations

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I have disclosed that the combination of MoO2(acac)2, (Ph3P)AuCl, and AgOTf provides a powerful catalytic system for the rapid 1,3-rearrangement of propargyl alcohols. The reactions proceed at room temperature within 1 h in most cases to afford a variety of α,β-unsaturated carbonyl compounds in excellent yields. During the further study on its application to various substrates, it was found that the cationic gold-catalyzed intramolecular cyclizations of the propargyl alcohols having carbonyl, hydroxyl, or amino groups gave the heterocyclic compounds, such as 3(2H)-furanones, furanes, and pyrroles. A polymer-supported cationic gold compound was also synthesized and showed high reactivity. It was recovered quantitatively from the reaction mixture by simple filtration and reused for four runs.