Efficient and simple approaches towards direct oxidative esterification of alcohols

Chemistry. 2014 Nov 17;20(47):15618-24. doi: 10.1002/chem.201403786. Epub 2014 Oct 3.

Abstract

The present article describes novel oxidative protocols for direct esterification of alcohols. The protocols involve successful demonstrations of both "cross" and "self" esterification of a wide variety of alcohols. The cross-esterification proceeds under a simple transition-metal-free condition, containing catalytic amounts of TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy)/TBAB (tetra-n-butylammonium bromide) in combination with oxone (potassium peroxo monosulfate) as the oxidant, whereas the self-esterification is achieved through simple induction of Fe(OAc)2 /dipic (dipic=2,6-pyridinedicarboxylic acid) as the active catalyst under an identical oxidizing environment.

Keywords: alcohols; direct oxidative esterification; iron; mechanistic study; transition-metal-free.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry*
  • Catalysis
  • Cyclic N-Oxides / chemistry
  • Esterification
  • Ferrous Compounds / chemistry
  • Oxidation-Reduction
  • Picolinic Acids
  • Pyridines
  • Sulfuric Acids / chemistry

Substances

  • Alcohols
  • Cyclic N-Oxides
  • Ferrous Compounds
  • Picolinic Acids
  • Pyridines
  • Sulfuric Acids
  • potassium peroxymonosulfuric acid
  • dipicolinic acid
  • TEMPO