A Highly Efficient Cooperative Effect in an Acylation Catalyst Bearing Weak Lewis Base and Lewis Acid Sites

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  • Satoshi Kojima
    Department of Chemistry, Graduate School of Science, Hiroshima University
  • Narumi Banden
    Department of Chemistry, Graduate School of Science, Hiroshima University
  • Yohsuke Yamamoto
    Department of Chemistry, Graduate School of Science, Hiroshima University

抄録

<jats:title>Abstract</jats:title> <jats:p>Tetrakis(2-pyridyl)stannane (o-Py4Sn), which bears only weakly nucleophilic and Lewis basic pyridines, and a weakly acidic tetraaryltin moiety, was found to efficiently catalyze the reaction between acetic anhydride and alcohols. The reaction rate measurements using 1-phenylethanol show the catalytic activity of o-Py4Sn to be up to 20% of that of 4-(dimethylamino)pyridine (DMAP) and more than 100 times that of pyridine alone. Furthermore, the reaction using (t-BOC)2O was found to be comparable to that with DMAP, with o-Py4Sn being more selective. Thus, a highly efficient cooperative effect is operative with o-Py4Sn.</jats:p>

収録刊行物

  • Chemistry Letters

    Chemistry Letters 43 (8), 1266-1268, 2014-08

    Oxford University Press (OUP)

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