Base-Free Fluoride-Mediated Vinylation of Alcohols with Calcium Carbide

Abstract

Here, we demonstrate that the reaction between calcium carbide and aliphatic and benzyl alcohols does not require an additional base as a catalyst and can be effectively promoted by readily available potassium fluoride. Potassium fluoride acts as a phase-transferring reagent, activating the calcium hydroxide base released from the reaction of calcium carbide with water. Given this insight, we have developed a novel synthetic pathway for the construction of alkyl vinyl ethers.