Aerobic oxygenation of α-methylene ketones under visible-light catalysed by a CeNi3 complex with a macrocyclic tris(salen)-ligand

Haruki Nagae; Kazutaka Sakamoto; Sakiko Fujiwara; Tobias Schindler; Yoshihiro Kon; Kazuhiko Sato; Jun Okuda; Kazushi Mashima

doi:10.1039/D1CC04540G

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Aerobic oxygenation of α-methylene ketones under visible-light catalysed by a CeNi₃ complex with a macrocyclic tris(salen)-ligand†

Haruki Nagae,

^a Kazutaka Sakamoto,

^a Sakiko Fujiwara,^a Tobias Schindler,^b Yoshihiro Kon,

^c Kazuhiko Sato,

*^c Jun Okuda

*^b and Kazushi Mashima

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka 560-8531, Japan
E-mail: mashima@chem.es.osaka-u.ac.jp

^b Institute of Inorganic Chemistry, RWTH Aachen University, Landoltweg 1, Aachen D-52062, Germany

^c Interdisciplinary Research Center for Catalytic Chemistry, National Institute of Advanced Industrial Science and Technology (AIST), Central 5, Tsukuba, Ibaraki 305-8565, Japan

Abstract

A hetero-tetranuclear CeNi₃ complex with a macrocyclic ligand catalysed the aerobic oxygenation of a methylene group adjacent to a carbonyl group under visible-light radiation to produce the corresponding α-diketones. The visible-light induced homolysis of the Ce–O bond of a bis(enolate) intermediate is proposed prior to aerobic oxygenation.

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Article information

DOI: https://doi.org/10.1039/D1CC04540G
Article type: Communication
Submitted: 17 Aug 2021
Accepted: 26 Sep 2021
First published: 28 Sep 2021

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Chem. Commun., 2021,57, 11169-11172

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Aerobic oxygenation of α-methylene ketones under visible-light catalysed by a CeNi₃ complex with a macrocyclic tris(salen)-ligand

H. Nagae, K. Sakamoto, S. Fujiwara, T. Schindler, Y. Kon, K. Sato, J. Okuda and K. Mashima, Chem. Commun., 2021, 57, 11169 DOI: 10.1039/D1CC04540G

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Chemical Communications