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Chromium–Salen Complex / Nitroxyl Radical Cooperative Catalysis:A New Combination for Aerobic Intramolecular Dearomative Coupling of Phenols

preprint
submitted on 07.09.2020 and posted on 07.09.2020 by Shota Nagasawa, Shogo Fujiki, Yusuke Sasano, Yoshiharu Iwabuchi
Herein we describe an aerobic intramolecular dearomative coupling reaction of phenols using a catalytic system with the combination of a chromium–salen (Cr–salen) complex and a nitroxyl radical. This novel catalytic system enables the construction of a spirocyclic dienone product, which is a potentially useful intermediate for the synthesis of various natural products such as alkaloids and phenylpropanoids from bisphenol in good yield under mild reaction conditions (under O2 and ambient temperature). A preliminary mechanistic study suggests that this reaction system is promoted by a cooperative electron transfer between the Cr(III)–salen complex, nitroxyl radical and bisphenol substrate.

Funding

JSPS KAKENHI 16K15096, 18H04232 19H03347

Platform Project for Supporting Drug Discovery and Life Science Research [Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)] from AMED JP18am0101100.

History

Email Address of Submitting Author

y-iwabuchi@m.tohoku.ac.jp

Institution

Tohoku University

Country

Japan

ORCID For Submitting Author

0000-0002-0679-939X

Declaration of Conflict of Interest

no conflict of interest

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