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Adaptive Photochemical Amination via Co(II) Catalysis
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    Adaptive Photochemical Amination via Co(II) Catalysis
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    • Geyang Song
      Geyang Song
      Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710062, China
      More by Geyang Song
    • Jiameng Song
      Jiameng Song
      Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710062, China
      More by Jiameng Song
    • Qi Li
      Qi Li
      Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710062, China
      More by Qi Li
    • Tengfei Kang
      Tengfei Kang
      Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710062, China
      More by Tengfei Kang
    • Jianyang Dong
      Jianyang Dong
      Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710062, China
    • Gang Li
      Gang Li
      Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710062, China
      More by Gang Li
    • Juan Fan
      Juan Fan
      Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710062, China
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    • Chao Wang
      Chao Wang
      Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710062, China
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    • Dong Xue*
      Dong Xue
      Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710062, China
      *Email: [email protected]
      More by Dong Xue
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2024, 146, 39, 26936–26946
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    https://doi.org/10.1021/jacs.4c08130
    Published September 18, 2024
    Copyright © 2024 American Chemical Society

    Abstract

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    Transition-metal-catalyzed amination of aryl halides is one of the most employed methods for constructing N-arylation adducts. However, the broad success of these reactions largely relies on the screening of precatalysts, elaborated ligands, and case-by-case optimization of reaction conditions (solvent, base, additive, temperature, etc.) for electronically or structurally diverse nucleophiles. Herein, we report an adaptive photochemical C–N coupling of aryl halides with various nitrogen nucleophiles (aliphatic and aromatic amines, amides, sulfonamides, pyrazoles, and ammonium salts) by Co(II) catalysis under the same reaction conditions (same precatalyst, same ligand, same base, same solvent, same temperature) without the addition of any exogenous photocatalyst. This photochemical amination features a wide substrate scope (>130 examples, up to 95% yield) with excellent functional group tolerance. Mechanistic studies indicate that these C–N coupling reactions may proceed via a Co(I)/Co(III) catalytic cycle.

    Copyright © 2024 American Chemical Society

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    This article is cited by 1 publications.

    1. Jianbin Li, Ding Zhang, Zhennan Hu. Ligand-Enabled “Two-in-One” Metallaphotocatalytic Cross Couplings. ACS Catalysis 2025, 15 (3) , 1635-1654. https://doi.org/10.1021/acscatal.4c07128

    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2024, 146, 39, 26936–26946
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.4c08130
    Published September 18, 2024
    Copyright © 2024 American Chemical Society

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