4.6 Article

Rh-Catalyzed Direct Amination of Unactivated C(sp3)-H bond with Anthranils Under Mild Conditions

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 32, Pages 11165-11169

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201602556

Keywords

amination; anthranils; C-H activation; heterocycles; rhodium

Funding

  1. National Basic Research Program of China (973 Program) [2015CB856600]
  2. National Natural Science Foundation of China [21325206]
  3. National Young Top-notch Talent Support Program

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C-N Bond formation is of great significance due to the ubiquity of nitrogen-containing compounds. Here, a mild and efficient RhIII-catalyzed C(sp(3))-H aryl amination reaction is reported. Anthranil is employed as the nitrogen source with 100% atom efficiency. This C-H amination reaction exhibits broad substrate scope without using any external oxidants. Mechanistic studies including rhodacycle intermediates, H-D exchange, kinetic isotope effect (KIE) experiments, and in situ IR are presented.

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