Utilization of Donor–Acceptor Interactions for the Catalytic Acceleration of Nucleophilic Additions to Aromatic Carbonyl Compounds

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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.
Funding Information
  • Japan Society for the Promotion of Science (15H05800)

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