Synthesis of Arylallenes by Palladium-Catalyzed Retro-Propargylation of Homopropargyl Alcohols

Abstract

Treatment of tertiary homopropargyl alcohol with aryl halide under palladium catalysis provided arylallenes regioselectively. The reaction includes retro-propargylation, which proceeds in a concerted fashion via a cyclic transition state and transfers the stereochemistry of homopropargyl alcohols through C-C bond cleavage. The present method enables the use of homopropargyl alcohols as allenylmetal equivalents.