Mild reaction conditions for the terminal deuteration of alkynes

Org Lett. 2012 Jan 20;14(2):456-9. doi: 10.1021/ol2029178. Epub 2012 Jan 11.

Abstract

Routinely employed syntheses of terminally deuterated alkynes often utilize strong bases (i.e., LDA, n-BuLi, or Grignard reagents) or low (i.e., -78 °C) or elevated (i.e., 56 °C) reaction temperatures; furthermore many of these procedures afford average yields and in some cases less than optimum deuterium incorporation. Herein we report the application of alternative extremely mild reaction conditions that readily afford quantitative yields of terminally deuterated alkynes in a matter of minutes with exceptional isotope incorporation at ambient temperature.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Alkynes / chemistry*
  • Amino Acids / chemistry
  • Anti-Bacterial Agents / chemical synthesis
  • Aziridines / chemical synthesis
  • Carbohydrates / chemistry
  • Cefazolin / chemical synthesis
  • Molecular Structure
  • Stereoisomerism

Substances

  • Alkynes
  • Amino Acids
  • Anti-Bacterial Agents
  • Aziridines
  • Carbohydrates
  • aziridine
  • Cefazolin