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Chinese Journal of Organic Chemistry >

2025 , Vol. 45 >Issue 4: 1047 - 1096

DOI: https://doi.org/10.6023/cjoc202408019

REVIEWS

Progress in N-α-C(sp3)—H Bond Functionalization for the Synthesis of N-Heterocycles

  • Yulan Fan ,
  • Xiaoying Zou ,
  • Xiaoqing Zhu ,
  • Lüyin Zheng ,
  • Wei Guo
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  • Jiangxi Provincial Key Laboratory of Synthetic Pharmaceutical Chemistry, College of Chemistry and Chemical Engineering, Gannan Normal University, Ganzhou, Jiangxi 341000
* E-mail: ;

Received date: 2024-08-15

  Revised date: 2024-09-20

  Online published: 2024-11-08

Supported by

National Natural Science Foundation of China(22167002); National Natural Science Foundation of China(22467001)

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Abstract

C(sp3)—H bond functionalization is currently a research hotspot in the field of organic synthesis. The delocalization effect between lone-pair electrons on the nitrogen atom in the N-α-C(sp3)—H bond with the electrons in single occupied molecular orbital (SOMO) of the neighboring carbon radical can reduce the dissociation energy of the C(sp3)—H bond, which facilitates the introduction of various nucleophilic or dipolar reagents into N-α-C(sp3) to provide a variety of nitrogen-contain- ing heterocyclic compounds with diverse structures through intermolecular or intramolecular nucleophilic annulation or dipole cyclization reactions. The research progress in N-α-C(sp3)—H bond functionalization for the synthesis of nitrogen-containing heterocyclic compounds under different conditions through the formation of iminium ions, α-aminoalkyl radicals, and azomethimine ylide intermediates is summarized. The possible reaction processes and their potential applications are discussed.

Key words： N-α-C(sp3)—H bond; iminium ions; α-aminoalkyl radicals; azomethimine ylides; N-heterocycles

Cite this article

Yulan Fan , Xiaoying Zou , Xiaoqing Zhu , Lüyin Zheng , Wei Guo . Progress in N-α-C(sp3)—H Bond Functionalization for the Synthesis of N-Heterocycles[J]. Chinese Journal of Organic Chemistry, 2025 , 45(4) : 1047 -1096 . DOI: 10.6023/cjoc202408019

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