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

Uchikura Tatsuhiro | Zendy; Ono Kosuke | Zendy; Takahashi Kohei | Zendy; Iwasawa Nobuharu | Zendy

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

Author(s) -

Uchikura Tatsuhiro,

Ono Kosuke,

Takahashi Kohei,

Iwasawa Nobuharu

Publication year - 2018

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201711726

Subject(s) - chemistry , ketene , nucleophile , electrophile , catalysis , silylation , electrophilic aromatic substitution , acceptor , medicinal chemistry , acetal , electron acceptor , substrate (aquarium) , photochemistry , nucleophilic addition , combinatorial chemistry , organic chemistry , physics , oceanography , geology , condensed matter physics

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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