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

Bo Dong, Weiguan Qi, Yifeng Chen, Yufei Zhang, Shiyu Gu, Jianlin Zhao, Qingfa Zhou, Jian Shen, Lan‐Gui Xie

2024Advanced Science12 citationsDOIOpen Access PDF

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.

Topics & Concepts

PeptideRadicalAmino acidCombinatorial chemistryChemistryMoleculeSurface modificationCarbon fibersPeptide synthesisOrganic chemistryMaterials scienceBiochemistryComposite materialPhysical chemistryComposite numberRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques