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Issue 16, 2018
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A copper/O2-mediated direct sp3 C–H/N–H cross-dehydrogen coupling reaction of acylated amines and N-aryl glycine esters

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Abstract

A copper salt-catalyzed cross-dehydrogenative coupling reaction between N-aryl glycine esters and acylated amines has been developed. The reaction proceeded effectively under an oxygen atmosphere without the use of peroxide agents. This simple protocol allows for the preparation of a series of new compounds in a moderate to excellent yield via the CDC reaction of a wide range of N-aryl glycine derivatives with acylated amines, which are of great interest in the field of medicinal chemistry. A plausible mechanism involving the formation of an iminium ion intermediate, followed by coupling with acylated amines was proposed after some control experiments were conducted.

Graphical abstract: A copper/O2-mediated direct sp3 C–H/N–H cross-dehydrogen coupling reaction of acylated amines and N-aryl glycine esters

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Publication details

The article was received on 21 Jan 2018, accepted on 22 Mar 2018 and first published on 23 Mar 2018


Article type: Paper
DOI: 10.1039/C8OB00176F
Citation: Org. Biomol. Chem., 2018,16, 2902-2909
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    A copper/O2-mediated direct sp3 C–H/N–H cross-dehydrogen coupling reaction of acylated amines and N-aryl glycine esters

    B. Sun, Y. Wang, D. Li, C. Jin and W. Su, Org. Biomol. Chem., 2018, 16, 2902
    DOI: 10.1039/C8OB00176F

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