Decarboxylative Acetoxylation of Aliphatic Carboxylic Acids

J Org Chem. 2019 Oct 4;84(19):12553-12561. doi: 10.1021/acs.joc.9b02092. Epub 2019 Sep 24.

Abstract

Organic molecules bearing acetoxy moieties are important functionalities in natural products, drugs, and agricultural chemicals. Synthesis of such molecules via transition metal-catalyzed C-O bond formation can be achieved in the presence of a carefully chosen directing group to alleviate the challenges associated with regioselectivity. An alternative approach is to use ubiquitous carboxylic acids as starting materials and perform a decarboxylative coupling. Herein, we report conditions for a photocatalytic decarboxylative C-O bond formation reaction that provides rapid and facile access to the corresponding acetoxylated products. Mechanistic investigations suggest that the reaction operates via oxidation of the carboxylate followed by rapid decarboxylation and oxidation by Cu(OAc)2.

Publication types

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

MeSH terms

  • Acetates / chemical synthesis*
  • Acetates / chemistry
  • Carboxylic Acids / chemistry*
  • Decarboxylation
  • Molecular Structure

Substances

  • Acetates
  • Carboxylic Acids