Issue 46, 2017

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

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

Supplementary files

Article information

Article type
Paper
Submitted
07 Sep 2017
Accepted
26 Oct 2017
First published
26 Oct 2017

Org. Biomol. Chem., 2017,15, 9875-9879

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, 15, 9875 DOI: 10.1039/C7OB02249B

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements