4.7 Article

Palladium-Catalyzed C-N Bond Cleavage of 2H-Azirines for the Synthesis of Functionalized α-Amido Ketones

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 4, Pages 2200-2208

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b03193

Keywords

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Funding

  1. National Natural Science Foundation of China [21701148, 21471134, 21571158]
  2. Key Research Project of University of Henan Province [19zx004]
  3. Universities in Henan Province [17A150053]

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A Pd-catalyzed ring-opening reaction of 2H-azirines with carboxylic acids was developed. This reaction undergoes nucleophilic addition between 2,3-diaryl-2H-azirines and carboxylic acids followed by C-N single-bond cleavage and a subsequent thermal rearrangement. This method enables the rapid construction of valuable alpha-amido ketone derivatives with high atomic efficiency and superb functional group tolerance.

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