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

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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Publication Details

Journal
Organic Letters
Published
2025-08-28
DOI
https://doi.org/10.1021/acs.orglett.5c03331
Citations
7
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
6.55

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article

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

Jingping Qü, Xianqing Wu, Yifeng Chen, Qinglin Wang et al.
7 citations
Organic Letters
Radical Photochemical Reactions
6.55
article

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

Jingping Qü, Xianqing Wu, Yifeng Chen, Qinglin Wang, Jiahao Bai
article en
7 citations

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.

Organic LettersVol. 27(36)
East China University of Science and Technology (CN), Chinese Academy of Sciences (CN), Shanghai Institute of Organic Chemistry (CN), Henan Normal University (CN)
National Natural Science Foundation of China, Science and Technology Commission of Shanghai Municipality, China Petrochemical Corporation, Project 211, Fundamental Research Funds for the Central Universities
Clean water and sanitation
Openalex Percentile: Top 3%
Radical Photochemical Reactions
6.55
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Iron-Catalyzed Radical Addition Reaction of Dehydroglycine with Aliphatic Carboxylic Acids — Jingping Qü, Xianqing Wu, et al. · Organic Letters (2025) | TGRS Research Map | TGRS