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Regiocontrolled Palladium-Catalyzed Arylative Cyclizations of Alkynols

Daishi Fujino, Hideki Yorimitsu* and Atsuhiro Osuka

*Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan, Email: yorikuchem.kyoto-u.ac.jp

D. Fujino, H. Yorimitsu, A. Osuka, J. Am. Chem. Soc., 2014, 136, 6255-6258.

DOI: 10.1021/ja502275w (free Supporting Information)


Abstract

Tuning the reactivity of arylpalladium intermediates enables 5-exo and 6-endo cyclizations of alkynols. These palladium-catalyzed reactions offer a divergent synthesis of oxygen-containing heterocycles, which are of synthetic use for further derivatization. Formal synthesis of an hNK-1 receptor antagonist also showcases the utility this arylative cyclization.

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Key Words

3,4-dihydro-2H-pyrans, tetrahydrofurans


ID: J48-Y2014