Metal-free synthesis of aryl esters from carboxylic acids and diaryliodonium salts

Org Lett. 2011 Jul 1;13(13):3462-5. doi: 10.1021/ol2012082. Epub 2011 May 26.

Abstract

An efficient arylation of carboxylic acids with diaryliodonium salts has been developed, giving aryl esters in high yields within short reaction times for both aromatic and aliphatic substrates. The transition-metal-free conditions are compatible with a range of functional groups, and good chemoselectivity is observed with unsymmetric diaryliodonium salts. Furthermore, steric hindrance in the ortho positions is well tolerated both in the carboxylic acid and in the diaryliodonium salt, yielding aryl esters that cannot be obtained via other esterification protocols.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anions / chemistry
  • Carboxylic Acids / chemistry*
  • Esters / chemical synthesis*
  • Molecular Structure
  • Onium Compounds / chemistry*

Substances

  • Anions
  • Carboxylic Acids
  • Esters
  • Onium Compounds