4.7 Article

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

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 5, Issue 19, Pages 2860-2863

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c8qo00794b

Keywords

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Funding

  1. NSFC [21772163, 21778042, 21375113]
  2. NFFTBS [J1310024]
  3. Fundamental Research Funds for the Central Universities [20720160030]

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The first amidation of tertiary arylamines with nitriles via a cascade dehydrogenation/heterocoupling/addition reaction between -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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