摘要：Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering

转自：康龙化成

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

Qinglin Wang, Jiahao Bai, Xianqing Wu,*Jingping Qu, and Yifeng Chen*

Key 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, Shanghai 200237, China;

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China; School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China;

—Org. Lett. 2025, 10.1021/acs.orglett.5c03331

KEYWORDS:Photochemistry, Fecatalysis (反应类型), alkyl carboxylic acids,dehydroglycines, aldimines (原料), amino acid (产物), C(sp3)- C(sp3) (成键类型), ligand-to-metal charge transfer (LMCT) (其他)

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 dehydroglycinederivatives. 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.

Background:Iron-Catalyzed C−C Bond Formation via LMCT Mediated

Decarboxylation

Condition Screening

Yifeng Chen and co-worker established a photoredox / ironcatalyzedaddition reaction of aldimines with various aliphatic carboxylic acids via a LMCT process. This method provides straightforward access to structurally diverse amino acid derivatives in excellent yields, leveraging the inherent advantages of readily available carboxylic acid feedstocks without prefunctionalization requirements. This radical addition protocol features with broad substrate scope, encompassing primary, secondary, tertiary, benzylic, and bioactive carboxylic acid.

来源：新浪财经