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Cu-catalyzed oxygenation of alkene-tethered amides with O2 via unactivated C[double bond, length as m-dash]C bond cleavage: a direct approach to cyclic imides

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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 C[double bond, length as m-dash]C 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.

Graphical abstract: Cu-catalyzed oxygenation of alkene-tethered amides with O2 via unactivated C [[double bond, length as m-dash]] C bond cleavage: a direct approach to cyclic imides

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Publication details

The article was received on 27 Jun 2019, accepted on 04 Aug 2019 and first published on 06 Aug 2019


Article type: Edge Article
DOI: 10.1039/C9SC03175H
Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY license
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    Cu-catalyzed oxygenation of alkene-tethered amides with O2 via unactivated C[double bond, length as m-dash]C bond cleavage: a direct approach to cyclic imides

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

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