Water as a Reactant: DABCO-Catalyzed Hydration of Activated Alkynes for the Synthesis of Divinyl Ethers

Abstract

A practical and efficient addition of water to readily available activated alkynes delivering divinyl ethers is reported. The reaction proceeds with full atom economy in a very straightforward experimental procedure. Additionally, of all the tertiary amines studied to catalyze the reaction, the best and most efficient is clearly DABCO (1,4-diazabicyclo[2.2.2]octane). Finally, the solvent choice is crucial for the efficiency of this process and we have found that the reaction is best performed in wet dichloromethane for propiolic esters and alkynones, and in wet acetonitrile for propiolamides.