Palladium‐Catalyzed Ring‐Opening of 2‐Alkylidenecyclobutanols: Stereoselective Synthesis of γ,δ‐Unsaturated Ketones by C−C Bond Cleavage

Abstract A facile synthesis of γ,δ‐unsaturated ketones via palladium‐catalyzed ring‐opening of 2‐alkylidenecyclobutanols with organic halides is described. The key step involves − bond cleavage via palladium‐catalyzed β‐carbon elimination. The desired γ,δ‐unsaturated ketones are obtained in good to excellent yields and broad functional group tolerability. Aryl, heteroaryl, benzyl, and alkynyl halides all readily participate to forge tri‐substituted carbon‐carbon double bond in a stereoselective manner. magnified image