Ozonolysis of unsaturated organotrifluoroborates

J Org Chem. 2007 Apr 27;72(9):3558-60. doi: 10.1021/jo070130r. Epub 2007 Apr 5.

Abstract

Organotrifluoroborates are robust reagents capable of withstanding ozonolysis of remote alkenes, thus providing a new route to oxo-substituted organotrifluoroborates. The primary ozonides initially generated upon ozonolysis can be reduced with Zn/AcOH to afford the carbonyl compounds. Alternatively, capture of the carbonyl oxides with either an appropriate N-oxide or H2O easily gives the desired oxo-substituted organotrifluoroborates. Both unsaturated alkyltrifluoroborates and aryltrifluoroborates effectively participate in the reaction. The process provides oxo-functionalized organotrifluoroborates that cannot be prepared directly via either transmetalation or hydroboration protocols.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Borates / chemistry
  • Chemistry, Organic / methods*
  • Hydrocarbons, Fluorinated / chemistry*
  • Ozone / chemistry*

Substances

  • Borates
  • Hydrocarbons, Fluorinated
  • Ozone