Selenium-catalyzed intramolecular atom- and redox-economical transformation of o-nitrotoluenes into anthranilic acids

Yiming Li; Yuhong Wang; Tilong Yang; Zhenyang Lin; Xuefeng Jiang

doi:10.1039/D0GC04407E

Selenium-catalyzed intramolecular atom- and redox-economical transformation of o-nitrotoluenes into anthranilic acids†

Yiming Li,‡^a Yuhong Wang,‡^a Tilong Yang,‡^b Zhenyang Lin

*^b and Xuefeng Jiang

*^ac

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* Corresponding authors

^a Shanghai Key Laboratory of Green Chemistry and Chemical Process, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, P. R. China
E-mail: xfjiang@chem.ecnu.edu.cn

^b Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, P. R. China
E-mail: chzlin@ust.hk

^c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. China

Abstract

Anthranilic acids (AAs) are significant basic chemicals used in pharmaceuticals, agrochemicals, dyes, fragrances, etc. Superfluous steps are always involved in obtaining AAs. Herein, we demonstrate a straightforward strategy to transform abundant o-nitrotoluenes into biologically and pharmaceutically significant AAs without any extra reductants, oxidants and protecting groups. Various sensitive groups, such as halogens, sulfide, aldehyde, pyridines, quinolines, etc., can be tolerated in this transformation. A hundred-gram-scale operation is realized efficiently with almost quantitative selenium recycling. Further mechanistic studies and DFT calculations disclosed the proposed atom-exchange processes and the key roles of the selenium species.

This article is part of the themed collection: 2021 Green Chemistry Hot Articles

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DOI: https://doi.org/10.1039/D0GC04407E
Article type: Paper
Submitted: 29 Dec 2020
Accepted: 22 Feb 2021
First published: 22 Feb 2021

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Green Chem., 2021,23, 2986-2991

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Selenium-catalyzed intramolecular atom- and redox-economical transformation of o-nitrotoluenes into anthranilic acids

Y. Li, Y. Wang, T. Yang, Z. Lin and X. Jiang, Green Chem., 2021, 23, 2986 DOI: 10.1039/D0GC04407E

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Green Chemistry

Selenium-catalyzed intramolecular atom- and redox-economical transformation of o-nitrotoluenes into anthranilic acids†

Abstract

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Selenium-catalyzed intramolecular atom- and redox-economical transformation of o-nitrotoluenes into anthranilic acids

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