Molecules (Mar 2024)

Radical Mediated Decarboxylation of Amino Acids via Photochemical Carbonyl Sulfide (COS) Elimination

  • Alby Benny,
  • Lorenzo Di Simo,
  • Lorenzo Guazzelli,
  • Eoin M. Scanlan

DOI
https://doi.org/10.3390/molecules29071465
Journal volume & issue
Vol. 29, no. 7
p. 1465

Abstract

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Herein, we present the first examples of amino acid decarboxylation via photochemically activated carbonyl sulfide (COS) elimination of the corresponding thioacids. This method offers a mild approach for the decarboxylation of amino acids, furnishing N-alkyl amino derivatives. The methodology was compatible with amino acids displaying both polar and hydrophobic sidechains and was tolerant towards widely used amino acid-protecting groups. The compatibility of the reaction with continuous-flow conditions demonstrates the scalability of the process.

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