Oxidative C(sp3)–H amidation of tertiary arylamines with nitriles

Binzhou Lin; Shanshan Shi; Yiqun Cui; Yupei Liu; Guo Tang; Yufen Zhao

doi:10.1039/C8QO00794B

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Oxidative C(sp³)–H amidation of tertiary arylamines with nitriles†

Binzhou Lin,^a Shanshan Shi,^a Yiqun Cui,^a Yupei Liu,^a Guo Tang

*^a and Yufen Zhao

^ab

Author affiliations

* Corresponding authors

^a Department of Chemistry, College of Chemistry and Chemical Engineering, and the Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen, Fujian 361005, China
E-mail: t12g21@xmu.edu.cn

^b Institute of Drug Discovery Technology, Ningbo University, Ningbo, Zhejiang 450052, China

Abstract

The first amidation of tertiary arylamines with nitriles via a cascade dehydrogenation/heterocoupling/addition reaction between α-C–H bonds of tertiary amines and nitrogen atoms of nitriles has been developed. The use of copper(I) iodide as a Lewis acid catalyst, N-hydroxyphthalimide as a free radical initiator, and 2,2,6,6-tetramethylpiperidine 1-oxyl as not only an oxidant but also a nucleophile enabled the conversion of tertiary aromatic amines with nitriles into secondary amides.

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Article information

DOI: https://doi.org/10.1039/C8QO00794B
Article type: Research Article
Submitted: 30 Jul 2018
Accepted: 31 Aug 2018
First published: 03 Sep 2018

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Org. Chem. Front., 2018,5, 2860-2863

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Oxidative C(sp³)–H amidation of tertiary arylamines with nitriles

B. Lin, S. Shi, Y. Cui, Y. Liu, G. Tang and Y. Zhao, Org. Chem. Front., 2018, 5, 2860 DOI: 10.1039/C8QO00794B

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