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Published on: August 12, 2019
Iron-Catalyzed Radical Addition Reaction of Dehydroglycine with Aliphatic Carboxylic Acids
Qinglin Wang1, Jiahao Bai1, Xianqing Wu1
1Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China.
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.
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