Stabilized Carbon Radical-Mediated Assembly of Arylthianthrenium Salts, Alkenes and Amino Acid/Peptide Derivatives

Adv Sci (Weinh). 2025 Jan;12(2):e2411579. doi: 10.1002/advs.202411579. Epub 2024 Nov 21.

Abstract

Efficiently assembling amino acids and peptides with bioactive molecules facilitates the modular and streamlined synthesis of a diverse library of peptide-related compounds. Particularly notable is their application in pharmaceutical development, leveraging site-selective late-stage functionalization. Here, a visible light-induced three-component reaction involving arylthianthrenium salts, amino acid/peptide derivatives, and alkenes are introduced. This approach utilizes captodatively-stabilized carbon radicals to enable radical-radical C─C coupling, effectively constructing complex bioactive molecules. This method offers a promising alternative route for modular synthesis of peptide-derived bio-relevant compounds.

Keywords: amino acid; captodative effect; late‐stage functionalization; radical coupling; thianthrenium salt.

MeSH terms

  • Alkenes* / chemistry
  • Amino Acids* / chemistry
  • Carbon* / chemistry
  • Free Radicals / chemistry
  • Peptides* / chemistry
  • Salts / chemistry

Substances

  • Alkenes
  • Amino Acids
  • Peptides
  • Carbon
  • Salts
  • Free Radicals