Functionalization of organotrifluoroborates: reductive amination

J Org Chem. 2008 May 16;73(10):3885-91. doi: 10.1021/jo800383e. Epub 2008 Apr 16.

Abstract

Herein we report the conversion of aldehyde-containing potassium and tetrabutylammonium organotrifluoroborates to the corresponding amines through reductive amination protocols. Potassium formate facilitated by catalytic palladium acetate, sodium triacetoxyborohydride, and pyridine borane have all served as effective hydride donors, reducing the initially formed imines or iminium ions to provide the corresponding amines.

Publication types

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

MeSH terms

  • Amination
  • Amines / chemical synthesis*
  • Amines / chemistry
  • Borates / chemistry*
  • Hydrocarbons, Fluorinated / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Stereoisomerism

Substances

  • Amines
  • Borates
  • Hydrocarbons, Fluorinated