Oxidative esterification of aldehydes using a recyclable oxoammonium salt

Org Lett. 2013 May 3;15(9):2222-5. doi: 10.1021/ol400785d. Epub 2013 Apr 24.

Abstract

A simple, high yielding, rapid route for the oxidative esterification of a wide range aldehydes to hexafluoroisopropyl (HFIP) esters using the oxoammonium salt 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (1a) is reported. These esters can be readily transformed into a variety of other functional groups. The spent oxidant (1b) can be recovered and conveniently reoxidized to regenerate the oxoammonium salt, 1a.

Publication types

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

MeSH terms

  • Aldehydes / chemistry*
  • Borates / chemistry*
  • Esterification
  • Molecular Structure
  • Oxidation-Reduction
  • Piperidines / chemistry*
  • Quaternary Ammonium Compounds / chemistry*
  • Salts / chemistry*

Substances

  • 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate
  • Aldehydes
  • Borates
  • Piperidines
  • Quaternary Ammonium Compounds
  • Salts