4.7 Article

Electrochemically Oxidative α-C-H Functionalization of Ketones: A Cascade Synthesis of α-Amino Ketones Mediated by NH4I

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 23, Pages 11565-11573

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b01595

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Funding

  1. National Natural Science Foundation of China [21272021, 21472011]
  2. national key research and development program [2016YFD0400801]

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An efficient electrochemical protocol for the synthesis of alpha-amino ketones via the oxidative cross-dehydrogenative coupling of ketones and secondary amines has been developed. The electrochemistry performs in a simple undivided cell using NH4I as a redox catalyst and a cheap graphite plate as electrodes under constant current conditions. Gram-scale reaction demonstrates the practicality of the protocol. The reaction is proposed to procced through an initial a-iodination of ketone, followed by a nucleophilic substitution of amines.

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