Synthesis of functionalized organotrifluoroborates via the 1,3-dipolar cycloaddition of azides

Org Lett. 2006 Jun 22;8(13):2767-70. doi: 10.1021/ol060826r.

Abstract

[reaction: see text] We have successfully prepared potassium azidoalkyltrifluoroborates from the corresponding halogen compounds in 94-98% yields through a nucleophilic substitution reaction with NaN(3). In the presence of various alkynes and Cu(I) as a catalyst, these azidotrifluoroborates easily formed 1,4-disubstituted organo-[1,2,3]-triazol-1-yl-trifluoroborates in 85-98% yields. This method was then developed into a facile one-pot synthesis for the preparation of various organo-[1,2,3]-triazol-1-yl-trifluoroborates using haloalkyltrifluoroborates as the starting materials.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry
  • Azides / chemistry*
  • Borates / chemical synthesis*
  • Combinatorial Chemistry Techniques*
  • Copper / chemistry
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Hydrocarbons, Fluorinated / chemistry*
  • Molecular Structure

Substances

  • Alkynes
  • Azides
  • Borates
  • Hydrocarbons, Fluorinated
  • Copper