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

Tatsuhiro Uchikura; Kosuke Ono; Kohei Takahashi; Nobuharu Iwasawa

doi:10.1002/anie.201711726

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

Angew Chem Int Ed Engl. 2018 Feb 19;57(8):2130-2133. doi: 10.1002/anie.201711726. Epub 2018 Jan 26.

Authors

Tatsuhiro Uchikura¹, Kosuke Ono^{1

2}, Kohei Takahashi¹, Nobuharu Iwasawa¹

Affiliations

¹ Department of Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8551, Japan.
² Present address: Department of Chemistry, Faculty of Science, Tokyo University of Science, Tokyo, 162-8601, Japan.

PMID: 29314440
DOI: 10.1002/anie.201711726

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.

Keywords: carbonyl compounds; donor-acceptor systems; host-guest systems; supramolecular chemistry.

Publication types

Research Support, Non-U.S. Gov't