Visible light-promoted CO2 fixation with imines to synthesize diaryl α-amino acids

Nat Commun. 2018 Nov 22;9(1):4936. doi: 10.1038/s41467-018-07351-2.

Abstract

Light-mediated transformations with CO2 have recently attracted great attention, with the focus on CO2 incorporation into C-C double and triple bonds, organohalides and amines. Herein is demonstrated visible light -mediated umpolung imine reactivity capable of engaging CO2 to afford α-amino acid derivatives. By employing benzophenone ketimine derivatives, CO2 fixation by hydrocarboxylation of C=N double bonds is achieved. Good to excellent yields of a broad range of α,α-disubstituted α-amino acid derivatives are obtained under mild conditions (rt, atmospheric pressure of CO2, visible light). A procedure that avoids tedious chromatographic purification and uses sustainable sunlight is developed to highlight the simplicity of this method.

Publication types

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

MeSH terms

  • Amino Acids, Aromatic / chemical synthesis
  • Amino Acids, Aromatic / chemistry*
  • Benzophenones / chemistry
  • Carbon Dioxide / chemistry*
  • Catalysis / radiation effects
  • Imines / chemistry*
  • Light*
  • Models, Chemical
  • Molecular Structure
  • Nitriles / chemistry
  • Photochemical Processes / radiation effects

Substances

  • Amino Acids, Aromatic
  • Benzophenones
  • Imines
  • Nitriles
  • ketimine
  • Carbon Dioxide
  • benzophenone