Utilization of Donor–Acceptor Interactions for the Catalytic Acceleration of Nucleophilic Additions to Aromatic Carbonyl Compounds |
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| Authors: | Tatsuhiro Uchikura Dr Kosuke Ono Dr Kohei Takahashi Prof Nobuharu Iwasawa |
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| Institution: | 1. Department of Chemistry, Tokyo Institute of Technology, Tokyo, Japan;2. Present address: Department of Chemistry, Faculty of Science, Tokyo University of Science, Tokyo, Japan |
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| Abstract: | A conceptually new method for the catalytic electrophilic activation of aromatic carbonyl substrates, by utilizing donor–acceptor interactions between an electron‐deficient macrocyclic boronic ester host ( 2+2] BTH‐F ) and an aromatic carbonyl guest substrate, was realized. In the presence of a catalytic amount of 2+2] BTH‐F , dramatic acceleration of the nucleophilic addition of a ketene silyl acetal towards either electron‐rich aromatic aldehydes or ketones was achieved. Several control experiments confirmed that inclusion of the aromatic substrates within 2+2] BTH‐F , through efficient donor–acceptor interactions, is essential for the acceleration of the reaction. |
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| Keywords: | carbonyl compounds donor-acceptor systems host-guest systems supramolecular chemistry |
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