Cu-catalyzed oxygenation of alkene-tethered amides with O2via unactivated CC bond cleavage: a direct approach to cyclic imides

Junhua Li; Jialiang Wei; Bencong Zhu; Teng Wang; Ning Jiao

doi:10.1039/C9SC03175H

Cu-catalyzed oxygenation of alkene-tethered amides with O₂via unactivated CC bond cleavage: a direct approach to cyclic imides†

Junhua Li,^a Jialiang Wei,^a Bencong Zhu,^a Teng Wang^b and Ning Jiao

*^ac

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* Corresponding authors

^a State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100191, China
E-mail: jiaoning@pku.edu.cn

^b School of Chemistry, Beihang University, Xue Yuan Road 37, Beijing, China

^c State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

Abstract

The transformations of unactivated alkenes through C [double bond, length as m-dash] C bond double cleavage are always attractive but very challenging. We report herein a chemoselective approach to valuable cyclic imides by a novel Cu-catalyzed geminal amino-oxygenation of unactivated CC bonds. O₂ was successfully employed as the oxidant as well as the O-source and was incorporated into alkenyl amides via C [double bond, length as m-dash] C bond cleavage for the efficient preparation of succinimide or glutarimide derivatives. Moreover, the present strategy under simple conditions can be used in the late-stage modification of biologically active compounds and the synthesis of pharmaceuticals, which demonstrated the potential application.

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DOI: https://doi.org/10.1039/C9SC03175H
Article type: Edge Article
Submitted: 27 Jun 2019
Accepted: 04 Aug 2019
First published: 06 Aug 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2019,10, 9099-9103

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Cu-catalyzed oxygenation of alkene-tethered amides with O₂via unactivated CC bond cleavage: a direct approach to cyclic imides

J. Li, J. Wei, B. Zhu, T. Wang and N. Jiao, Chem. Sci., 2019, 10, 9099 DOI: 10.1039/C9SC03175H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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