9-Cyano-10-methoxycarbonylanthracene as a Visible Organic Photoredox Catalyst in the Two-Molecule Photoredox System

Yuka Tajimi; Yasuhiro Nachi; Ryoko Inada; Ryoga Hashimoto; Mugen Yamawaki; Kei Ohkubo; Toshio Morita; Yasuharu Yoshimi

doi:10.1021/acs.joc.2c00643

9-Cyano-10-methoxycarbonylanthracene as a Visible Organic Photoredox Catalyst in the Two-Molecule Photoredox System

J Org Chem. 2022 Jun 3;87(11):7405-7413. doi: 10.1021/acs.joc.2c00643. Epub 2022 May 23.

Authors

Yuka Tajimi¹, Yasuhiro Nachi¹, Ryoko Inada¹, Ryoga Hashimoto¹, Mugen Yamawaki², Kei Ohkubo^{3

4}, Toshio Morita¹, Yasuharu Yoshimi¹

Affiliations

¹ Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, University of Fukui, 3-9-1 Bunkyo, Fukui 910-8507, Japan.
² Department of Chemistry and Biology, National Institute of Technology, Fukui College, Genshi-cho, Fukui 916-8507, Japan.
³ Institute for Advanced Co-creation Studies, Osaka University, 2-8 Yamada-oka, Suita, Osaka 565-0871, Japan.
⁴ Institute for Open and Transdisciplinary Research Initiatives, Osaka University, 2-8 Yamada-oka, Suita, Osaka 565-0871, Japan.

PMID: 35604396
DOI: 10.1021/acs.joc.2c00643

Abstract

Visible-light-induced decarboxylative and deboronative reactions using two-molecule organic photoredox catalysts, namely, phenanthrene (Phen) and biphenyl (BP), as electron donors and 9-cyano-10-methoxycarbonylanthracene 1a as an electron acceptor were achieved. The high solubility of 1a significantly improved the reaction efficiency and product yield. In addition, the facile tuning of the oxidation potential of the electron-donor molecule via the replacement of Phen with BP enabled the application of the two-molecule photoredox system to a wide range of substrates.