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Copper nitrate-catalyzed oxidative coupling of unactivated C(sp3)–H bonds of ethers and alkanes with N-hydroxyphthalimide: synthesis of N-hydroxyimide esters

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Abstract

A copper nitrate-catalyzed cross-dehydrogenative coupling reaction between N-hydroxyphthalimide (NHPI) and ethers/alkanes has been described. The reaction is accomplished smoothly by using simple and green molecular oxygen as the oxidant, providing an alternative for the efficient synthesis of N-alkoxyphthalimides. In addition, it was found that when tert-butyl ethers were used as substrates, unexpected N-hydroxyimide ester derivatives were obtained in moderate to excellent yields. To further understand this unusual transformation, control experiments were performed and a plausible mechanism was proposed.

Graphical abstract: Copper nitrate-catalyzed oxidative coupling of unactivated C(sp3)–H bonds of ethers and alkanes with N-hydroxyphthalimide: synthesis of N-hydroxyimide esters

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Publication details

The article was received on 07 Sep 2017, accepted on 26 Oct 2017 and first published on 26 Oct 2017


Article type: Paper
DOI: 10.1039/C7OB02249B
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Copper nitrate-catalyzed oxidative coupling of unactivated C(sp3)–H bonds of ethers and alkanes with N-hydroxyphthalimide: synthesis of N-hydroxyimide esters

    X. Xu, J. Sun, Y. Lin, J. Cheng, P. Li, Y. Yan, Q. Shuai and Y. Xie, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB02249B

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