4.7 Article

Selective Cleavage of Inert Aryl C-N Bonds in N-Aryl Amides

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 3, Pages 1369-1376

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b02880

Keywords

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Funding

  1. NSFC [21272057, 21372065, 21772032, 21702051, U1604285]
  2. Natural Science Foundation of Henan [162300410180]
  3. Henan Provincial Natural Science Foundation [162300410180]
  4. Young Backbone Teachers Fund of Henan [2014GGJS-049]
  5. Science & Technology Innovation Talents in Universities of Henan [17HASTIT002]
  6. Henan Normal University [14YR002]
  7. Jilin Province Key Laboratory of Organic Functional Molecular Design Synthesis [130028742]

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A highly selective, IBX-promoted reaction has been developed for the oxidative cleavage of inert C(aryl)-N bonds on secondary amides while leaving the C(carbonyl)-N bond unchanged. This metal-free reaction proceeds under mild conditions (HFIP/H2O, 25 degrees C), providing facile access to various useful primary amides, some of which would be otherwise unattainable using conventional aminolysis and hydrolysis approaches.

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