Copper-catalyzed ortho-C(sp2)–H amination of benzamides and picolinamides with alkylamines using oxygen as a green oxidant

Qiong Li; Jie Huang; Gong Chen; Shui-Bo Wang

doi:10.1039/D0OB00784F

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Copper-catalyzed ortho-C(sp²)–H amination of benzamides and picolinamides with alkylamines using oxygen as a green oxidant†

Qiong Li,

*^a Jie Huang,^a Gong Chen

^b and Shui-Bo Wang^a

Author affiliations

* Corresponding authors

^a School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237, China
E-mail: qul16@ecust.edu.cn

^b State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China

Abstract

A versatile Cu-catalyzed direct ortho-C(sp²)–H amination of benzamides and picolinamides with alkylamines has been achieved. This method employs cheap and eco-friendly copper as a catalyst and oxygen as an oxidant, and also has the advantages of straightforward steps and excellent functional group compatibility. Further application of our approach was demonstrated by the synthesis of TCMDC-125116, SPHINX, and SRPIN340.

This article is part of the themed collections: Synthetic methodology in OBC and Catalysis & biocatalysis in OBC

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Article information

DOI: https://doi.org/10.1039/D0OB00784F
Article type: Paper
Submitted: 16 Apr 2020
Accepted: 04 Jun 2020
First published: 09 Jun 2020

Download Citation

Org. Biomol. Chem., 2020,18, 4802-4814

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Copper-catalyzed ortho-C(sp²)–H amination of benzamides and picolinamides with alkylamines using oxygen as a green oxidant

Q. Li, J. Huang, G. Chen and S. Wang, Org. Biomol. Chem., 2020, 18, 4802 DOI: 10.1039/D0OB00784F

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Organic & Biomolecular Chemistry