Thermodynamically Favorable Synthesis of 2-Oxazolidinones through Silver-Catalyzed Reaction of Propargylic Alcohols, CO2, and 2-Aminoethanols

ChemSusChem. 2016 Aug 23;9(16):2054-8. doi: 10.1002/cssc.201600470. Epub 2016 Jul 6.

Abstract

Development of catalytic routes to incorporate CO2 into carbonyl compounds at mild conditions remains attractive and challenging. Herein, a one-pot three-component cascade reaction of terminal propargylic alcohols, CO2 , and 2-aminoethanols through Ag(I) -based catalysis is reported for the synthesis of carbonyl compounds through C-O/C-N bond formation. This thermodynamically favorable route can be ingeniously regulated to afford a wide range of 2-oxazolidinones along with concurrent production of α-hydroxyl ketone derivatives in excellent yields and selectivity. Preliminary mechanistic studies indicate that such a process proceeds through successive formation of α-alkylidene cyclic carbonate, β-oxopropylcarbamate, and 2-oxazolidinones.

Keywords: carbon dioxide fixation; heterocycles; homogeneous catalysis; multicomponent reaction; synthetic methods.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Carbon Dioxide / chemistry*
  • Catalysis
  • Chemistry Techniques, Synthetic
  • Ethanolamine / chemistry*
  • Oxazolidinones / chemical synthesis*
  • Oxazolidinones / chemistry*
  • Propanols / chemistry*
  • Silver / chemistry*
  • Thermodynamics

Substances

  • Alkynes
  • Oxazolidinones
  • Propanols
  • Carbon Dioxide
  • Silver
  • Ethanolamine
  • propargyl alcohol