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- Title
Utilization of Donor–Acceptor Interactions for the Catalytic Acceleration of Nucleophilic Additions to Aromatic Carbonyl Compounds.
- Authors
Uchikura, Tatsuhiro; Ono, Kosuke; Takahashi, Kohei; Iwasawa, Nobuharu
- Abstract
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 (<bold>[2+2]</bold><italic><bold>BTH‐F</bold></italic>) and an aromatic carbonyl guest substrate, was realized. In the presence of a catalytic amount of <bold>[2+2]</bold><italic><bold>BTH‐F</bold></italic>, 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 <bold>[2+2]</bold><italic><bold>BTH‐F</bold></italic>, through efficient donor–acceptor interactions, is essential for the acceleration of the reaction.
- Subjects
ELECTRON donor-acceptor complexes; CATALYSIS; NUCLEOPHILIC addition (Chemistry); CARBONYL compounds; ACTIVATION (Chemistry)
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 8, p2152
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201711726