4.5 Article

Intermolecular Amination of Ketoximes with Anthranils by Rh-Catalyzed C-H Bond Activation in Air

Journal

ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 10, Issue 4, Pages 838-844

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202100043

Keywords

Rh-catalyzed; C2-Amination; C− H Activation; Ketoximes; Anthranils

Funding

  1. Natural Science Foundation of Shandong Province [ZR2020MB009, ZR2019MB009]
  2. Key Research and Development Program of Shandong Province [2019GSF108089]
  3. National Natural Science Foundation of China [21672046, 21372054]
  4. Huancui District of Weihai City

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The research developed a new method using [RhCp*Cl-2](2)/AgSbF6 system for C2-amination reaction between ketoximes and anthranils. Piv(2)O as a promoter played a key role in catalytic activity, and the oxime unit effectively activated the aryl C-H bond.
The formation of C-N bonds is a fundamental bond construction in organic synthesis. In this context, a [RhCp*Cl-2](2)/AgSbF6 system was developed for the C2-amination of ketoximes with anthranils with the use of Piv(2)O as a promoter. Piv(2)O played an important role in the generation of catalytically active species with [RhCp*Cl-2](2). The oxime unit was revealed to be effective chelating groups to activate the aryl C-H bond. The amination shows a wide substrates scope, and several important functional groups were tolerated under the benign reaction conditions.

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