Isoindolinone synthesis through Rh/Cu-catalyzed oxidative C–H/N–H annulation of N-methoxy benzamides with saturated ketones

Xiao Du; Yuntao Hu; Darun Yang; Decai Huang; Wendi Yang; Hailong Wu; Huaiqing Zhao

doi:10.1039/D1OB02166D

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Isoindolinone synthesis through Rh/Cu-catalyzed oxidative C–H/N–H annulation of N-methoxy benzamides with saturated ketones†

Xiao Du,^a Yuntao Hu,^a Darun Yang,^a Decai Huang,^a Wendi Yang,^a Hailong Wu^b and Huaiqing Zhao

*^a

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* Corresponding authors

^a School of Chemistry and Chemical Engineering, University of Jinan, Jinan, Shandong, P. R. China
E-mail: chm_zhaohq@ujn.edu.cn

^b School of Mechanical and Resource Engineering, Wuzhou University, Wuzhou, China

Abstract

The synthesis of isoindolinones from N-methoxy benzamides and saturated ketones via a bimetallic tandem catalytic annulation has been accomplished. The reaction is catalyzed by a Rh/Cu-cocatalytic system and proceeds via the combination of Cu-catalyzed dehydrogenation of ketones and Rh-catalyzed direct C–H functionalization with the assistance of the N-methoxy amide group which also acts as an oxidant to regenerate the Rh catalyst. This method shows good compatibility with a wide range of substrates and functional groups, and provides an alternative strategy to obtain diverse isoindolinones.

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Article information

DOI: https://doi.org/10.1039/D1OB02166D
Article type: Communication
Submitted: 04 Nov 2021
Accepted: 21 Dec 2021
First published: 21 Dec 2021

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Org. Biomol. Chem., 2022,20, 783-789

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Isoindolinone synthesis through Rh/Cu-catalyzed oxidative C–H/N–H annulation of N-methoxy benzamides with saturated ketones

X. Du, Y. Hu, D. Yang, D. Huang, W. Yang, H. Wu and H. Zhao, Org. Biomol. Chem., 2022, 20, 783 DOI: 10.1039/D1OB02166D

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Organic & Biomolecular Chemistry

Isoindolinone synthesis through Rh/Cu-catalyzed oxidative C–H/N–H annulation of N-methoxy benzamides with saturated ketones†

Abstract

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Isoindolinone synthesis through Rh/Cu-catalyzed oxidative C–H/N–H annulation of N-methoxy benzamides with saturated ketones

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