Catalytic Staudinger-Vilarrasa reaction for the direct ligation of carboxylic acids and azides

J Org Chem. 2009 Mar 6;74(5):2203-6. doi: 10.1021/jo802825e.

Abstract

2,2'-Dipyridyl diselenide (PySeSePy) is the catalyst or activator of choice for the direct reaction of carboxylic acids with azides and trimethylphosphine at room temperature. The mechanism of the process, which is not an aza-Wittig reaction, has been elucidated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 2,2'-Dipyridyl / analogs & derivatives*
  • 2,2'-Dipyridyl / chemistry
  • Amides / chemical synthesis*
  • Amides / chemistry
  • Azides / chemistry*
  • Carboxylic Acids / chemistry*
  • Catalysis
  • Molecular Structure
  • Organoselenium Compounds / chemistry*
  • Stereoisomerism

Substances

  • Amides
  • Azides
  • Carboxylic Acids
  • Organoselenium Compounds
  • 2,2'-Dipyridyl
  • 2,2'-dipyridyl diselenide