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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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Catalyst-Free Benzylic C(sp3)─H Bond Intermolecular Amination.

Wen Zhang1, Man Wang1, Hequan Yao1

  • 1State Key Laboratory of Natural Medicines (SKLNM) and Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical University, Nanjing, 211198, China.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|November 20, 2025
PubMed
Summary

This study introduces a green method for direct amination of benzylic C(sp3)−H bonds without metals, catalysts, or oxidants. The efficient process is scalable and works well with complex molecules.

Keywords:
C─H activationHydrogen atom transferaminationcatalyst‐free

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Area of Science:

  • Organic Chemistry
  • Green Chemistry
  • Catalysis

Background:

  • Direct functionalization of C(sp3)−H bonds is crucial in organic synthesis.
  • Developing environmentally friendly methods remains a key challenge.

Purpose of the Study:

  • To develop a sustainable and efficient method for direct amination of benzylic C(sp3)−H bonds.
  • To achieve this without using metals, photocatalysts, or oxidants.

Main Methods:

  • The study employed a novel reaction strategy for direct amination.
  • Conditions were optimized to be metal-free, photocatalyst-free, and oxidant-free.

Main Results:

  • The developed protocol demonstrated high efficiency and excellent functional group tolerance.
  • Successful gram-scale synthesis and late-stage functionalization of complex molecules were achieved.

Conclusions:

  • This work provides an environmentally benign and efficient approach for benzylic C(sp3)−H bond amination.
  • The method offers a scalable and versatile tool for synthesizing complex organic molecules.