Ester Formation via Symbiotic Activation Utilizing Trichloroacetimidate Electrophiles

J Org Chem. 2019 Jun 21;84(12):7871-7882. doi: 10.1021/acs.joc.9b00745. Epub 2019 May 30.

Abstract

Trichloroacetimidates are useful reagents for the synthesis of esters under mild conditions that do not require an exogenous promoter. These conditions avoid the undesired decomposition of substrates with sensitive functional groups that are often observed with the use of strong Lewis or Brønsted acids. With heating, these reactions have been extended to benzyl esters without electron-donating groups. These inexpensive and convenient methods should find application in the formation of esters in complex substrates.

Publication types

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

MeSH terms

  • Acetamides / chemistry*
  • Carboxylic Acids / chemistry
  • Chloroacetates / chemistry*
  • Electrons*
  • Esters / chemistry*

Substances

  • Acetamides
  • Carboxylic Acids
  • Chloroacetates
  • Esters
  • trichloroacetamide