Guanidine/Azole Binary System as an Efficient Catalyst for Morita–Baylis–Hillman Reaction

Authors

  • Prof. Dr. Masahiro Terada,

    Corresponding author
    1. Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578 (Japan), Fax: (+81) 22-795-6602
    2. Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578 (Japan)
    • Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578 (Japan), Fax: (+81) 22-795-6602
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  • Satoko Fukuchi,

    1. Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578 (Japan), Fax: (+81) 22-795-6602
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  • Kei Amagai,

    1. Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578 (Japan), Fax: (+81) 22-795-6602
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  • Dr. Megumi Nakano,

    1. Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578 (Japan), Fax: (+81) 22-795-6602
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  • Dr. Hitoshi Ube

    1. Department of Chemistry, Graduate School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
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Abstract

original image

A catalyst is more than ones and zeros: The efficient catalysis for the Morita–Baylis–Hillman reaction of aromatic aldehydes with cyclic enones was demonstrated using a binary catalytic system consisting of a guanidine derivative and an azole derivative. The present binary system is well embedded into the catalytic cycles to stabilize the anionic intermediates through the hydrogen-bonding interaction with the guanidinium ion.

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