Copper-Catalyzed Alkoxycarbonylation of Alkanes with Alcohols

ChemSusChem. 2017 Apr 10;10(7):1341-1345. doi: 10.1002/cssc.201601587. Epub 2016 Dec 21.

Abstract

Esters are important chemicals widely used in various areas, and alkoxycarbonylation represents one of the most powerful tools for their synthesis. In this communication, a new copper-catalyzed carbonylative procedure for the synthesis of aliphatic esters from cycloalkanes and alcohols was developed. Through direct activation of the Csp3 -H bond of alkanes and with alcohols as the nucleophiles, the desired esters were prepared in moderate-to-good yields. Paraformaldehyde could also be applied for in situ alcohol generation by radical trapping, and moderate yields of the corresponding esters could be produced. Notably, this is the first report on copper-catalyzed alkoxycarbonylation of alkanes.

Keywords: alcohols; alkanes; carbonylation; copper catalyst; esters.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry*
  • Alkanes / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Esters / chemical synthesis
  • Esters / chemistry
  • Ketones / chemistry
  • Palladium / chemistry

Substances

  • Alcohols
  • Alkanes
  • Esters
  • Ketones
  • Palladium
  • Copper