Issue 82, 2022
From the journal:

Chemical Communications

Regioselective peri-C–H selenylation of aromatic compounds with weakly coordinating ketone groups†

Bingbing Duan,a   Yao Wu,a   Yi Gao,a   Linkun Ying,a   Jielin Tang,a   Shiyu Hu,a   Qiuhua Zhao*b  and  Zengqiang Song ORCID logo *a  

* Corresponding authors

a School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou, Zhejiang, China
E-mail: songzengqiang09@163.com

b School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, China
E-mail: qhzhao@chem.ecnu.edu.cn

Abstract

A novel and versatile method for peri-C–H selenylation of aromatic compounds bearing ketone groups, including chromones, xanthones, acridinones, quinolinones and naphthoquinones with diselenides under Ru(II) catalysis is presented. Various chromones and diselenides are applicable for this transformation, affording 5-selenyl chromones in a highly regioselective manner in good to excellent yields. This transformation is easy to scale up and the desired products can be further modified. Most importantly, this transformation allows the late-stage selenylation of bioactive compounds. Mechanistic studies show that radicals may be involved in this novel transformation.

Graphical abstract: Regioselective peri-C–H selenylation of aromatic compounds with weakly coordinating ketone groups

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Article information

DOI
https://doi.org/10.1039/D2CC04030A
Article type
Communication
Submitted
19 Jul 2022
Accepted
17 Sep 2022
First published
20 Sep 2022

Chem. Commun., 2022,58, 11555-11558

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Regioselective peri-C–H selenylation of aromatic compounds with weakly coordinating ketone groups

B. Duan, Y. Wu, Y. Gao, L. Ying, J. Tang, S. Hu, Q. Zhao and Z. Song, Chem. Commun., 2022, 58, 11555 DOI: 10.1039/D2CC04030A

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