The nitrilimine-alkene cycloaddition is an ultra rapid click reaction

Chem Commun (Camb). 2014 Mar 25;50(24):3176-9. doi: 10.1039/c3cc48682f. Epub 2014 Feb 12.

Abstract

The transient formation of nitrilimine in aqueous conditions is greatly influenced by pH and chloride. In basic conditions (pH 10) with no chloride, a diarylnitrilimine precursor readily ionizes to form diarylnitrilimine that reacts almost instantly with an acrylamide-containing protein and fluorescently labels it.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkenes / chemistry*
  • Chlorides / chemistry
  • Click Chemistry
  • Cyclization
  • Hydrogen-Ion Concentration
  • Imines / chemical synthesis
  • Imines / chemistry*
  • Molecular Structure
  • Nitriles / chemistry*

Substances

  • Alkenes
  • Chlorides
  • Imines
  • Nitriles