Ruthenium-Catalyzed Transformation of Aryl and Alkynyl Propargyl Ethers into Aryl and Alkynyl Ketones via Cleavage of a Carbon−Carbon Triple Bond

Abstract

Treatment of aryl and alkynyl propargyl ethers with water and TpRuPPh3(CH3CN)2PF6 catalyst in hot dichloroethane led to the removal of the propargyl ether group and gave aryl and alkynyl ketones efficiently. Analysis of the gaseous mixture above the reaction solution showed the presence of carbon monoxide, ethylene, ethane, and carbon monoxide, produced from degradation of the propargyl ether functionality with water. A plausible reaction mechanism is proposed on the basis of reaction products. This catalytic reaction proves to be a reliable method to obtain aryl and alkynyl ketones from their propargyl ether derivatives.