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

Sayuri Hayashi, Koji Hirano, Hideki Yorimitsu* and Koichiro Oshima*

*Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto-daigaku Katsura, Nishikyo-ku, Kyoto 615-8510, Japan, Email:,

S. Hayashi, K. Hirano, H. Yorimitsu, K. Oshima, J. Am. Chem. Soc., 2008, 130, 5048-5049.

DOI: 10.1021/ja800986m (free Supporting Information)


Tertiary homopropargyl alcohols can be used as allenylmetal equivalents in a palladium-catalyzed reaction with aryl halides to provide 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.

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ID: J48-Y2008-1010