Copper Promoted Aerobic Oxidative C(sp3)-C(sp3) Bond Cleavage of N-(2-(Pyridin-2-yl)-ethyl)anilines

J Org Chem. 2020 Feb 21;85(4):2725-2732. doi: 10.1021/acs.joc.9b02919. Epub 2020 Jan 21.

Abstract

A strategy of aerobic oxidative C(sp3)-C(sp3) bond cleavage of N-ethylaniline derivatives bearing azaarenes for the synthesis of N-aryl formamides has been developed. This approach was carried out smoothly with the CuI/TEMPO/air system to give N-aryl formamides in yields of 50-90%. With this methodology, a mutagenically active compound was constructed in 90% yield. Moreover, the reaction also provided a one-pot synthetic tool for accessing a promoter of hematopoietic stem cells by difunctionalization in 61% yield.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aniline Compounds*
  • Catalysis
  • Copper*
  • Molecular Structure
  • Oxidative Stress

Substances

  • Aniline Compounds
  • Copper