Cs2CO3-promoted carboxylation of N-tosylhydrazones with carbon dioxide toward α-arylacrylic acids

J Org Chem. 2015 Mar 6;80(5):2855-60. doi: 10.1021/jo502908v. Epub 2015 Feb 25.

Abstract

A Cs2CO3-promoted carboxylation of N-tosylhydrazones and CO2 has been developed. The reaction proceeded efficiently at 80 °C under atmospheric CO2, gave the corresponding α-arylacrylic acids in moderate to good yields. This method was featured with (1) the employment of Cs2CO3 rather than (n)BuLi as the base; (2) a reaction temperature of 80 °C rather than -78 °C.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrylates / chemical synthesis*
  • Acrylates / chemistry*
  • Carbon Dioxide / chemistry*
  • Carbonates / chemistry*
  • Catalysis
  • Cesium / chemistry*
  • Molecular Structure
  • Organic Chemistry Phenomena
  • Temperature
  • Tosyl Compounds / chemical synthesis*
  • Tosyl Compounds / chemistry*

Substances

  • Acrylates
  • Carbonates
  • Tosyl Compounds
  • Carbon Dioxide
  • Cesium
  • cesium carbonate