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Iron-Catalyzed Radical Addition Reaction of Dehydroglycine with Aliphatic Carboxylic Acids

Qinglin Wang, Jiahao Bai, Xianqing Wu, Jingping Qü, Yifeng Chen

2025Organic Letters9 citationsDOI

Abstract

Iron-catalyzed ligand-to-metal charge transfer (LMCT) processes have emerged as robust strategies for diverse organic transformations. Despite this potential, their application to addition reactions of C═N unsaturated bonds remains underexplored. Herein, we report an LMCT-enabled, photoredox/iron-catalyzed radical addition to dehydroglycine derivatives. This method employs readily available aliphatic carboxylic acids as radical precursors, enabling direct decarboxylative addition for the efficient synthesis of structurally diverse amino acid derivatives in excellent yields (up to 99%) without prefunctionalization. The protocol exhibits broad scope, including successful late-stage functionalization of pharmaceutically relevant molecules.

Topics & Concepts

ChemistryCatalysisCarboxylic acidOrganic chemistryMedicinal chemistryRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods