Rh(I)-Catalyzed Coupling of Azides with Boronic Acids Under Neutral Conditions

Org Lett. 2022 Aug 5;24(30):5546-5551. doi: 10.1021/acs.orglett.2c02053. Epub 2022 Jul 26.

Abstract

Because of the importance of polyfunctional amines, C-N bond formation is important in synthetic organic chemistry. Here we present a neutral amination reaction using azides as the nitrogen source and arylboronic acids with a rhodium(I) catalyst to afford alkyl-aryl and aryl-aryl secondary amines. Natural products and pharmaceutical derivatives were applied, and gram-scale reactions were performed, which demonstrated the utility. Mechanistic experiments and DFT calculations suggested that the reaction involves a metal-nitrene intermediate.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amination
  • Amines / chemistry
  • Azides* / chemistry
  • Boronic Acids*
  • Catalysis

Substances

  • Amines
  • Azides
  • Boronic Acids