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Decarboxylative tandem C-N coupling with nitroarenes via SH2 mechanism

Author

Listed:
  • Shuaishuai Wang

    (School of Chemistry and Chemical Engineering, Nanjing University)

  • Tingrui Li

    (School of Chemistry and Chemical Engineering, Nanjing University)

  • Chengyihan Gu

    (School of Chemistry and Chemical Engineering, Nanjing University)

  • Jie Han

    (School of Chemistry and Chemical Engineering, Nanjing University)

  • Chuan-Gang Zhao

    (School of Chemistry and Chemical Engineering, Nanjing University)

  • Chengjian Zhu

    (School of Chemistry and Chemical Engineering, Nanjing University
    Shanghai Institute of Organic Chemistry
    College of Chemistry and Molecular Engineering, Zhengzhou University)

  • Hairen Tan

    (College of Engineering and Applied Sciences, Nanjing University)

  • Jin Xie

    (School of Chemistry and Chemical Engineering, Nanjing University
    Hunan University)

Abstract

Aromatic tertiary amines are one of the most important classes of organic compounds in organic chemistry and drug discovery. It is difficult to efficiently construct tertiary amines from primary amines via classical nucleophilic substitution due to consecutive overalkylation. In this paper, we have developed a radical tandem C-N coupling strategy to efficiently construct aromatic tertiary amines from commercially available carboxylic acids and nitroarenes. A variety of aromatic tertiary amines can be furnished in good yields (up to 98%) with excellent functional group compatibility under mild reaction conditions. The use of two different carboxylic acids also allows for the concise synthesis of nonsymmetric aromatic tertiary amines in satisfactory yields. Mechanistic studies suggest the intermediacy of the arylamine–(TPP)Fe(III) species and might provide a possible evidence for an SH2 (bimolecular homolytic substitution) pathway in the critical C-N bond formation step.

Suggested Citation

  • Shuaishuai Wang & Tingrui Li & Chengyihan Gu & Jie Han & Chuan-Gang Zhao & Chengjian Zhu & Hairen Tan & Jin Xie, 2022. "Decarboxylative tandem C-N coupling with nitroarenes via SH2 mechanism," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-30176-z
    DOI: 10.1038/s41467-022-30176-z
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    References listed on IDEAS

    as
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    2. Chi Wai Cheung & Xile Hu, 2016. "Erratum: Amine synthesis via iron-catalysed reductive coupling of nitroarenes with alkyl halides," Nature Communications, Nature, vol. 7(1), pages 1-1, December.
    3. Shashikant Dighe & Fabio Juliá & Alberto Luridiana & James J. Douglas & Daniele Leonori, 2020. "A photochemical dehydrogenative strategy for aniline synthesis," Nature, Nature, vol. 584(7819), pages 75-81, August.
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    5. Chi Wai Cheung & Xile Hu, 2016. "Amine synthesis via iron-catalysed reductive coupling of nitroarenes with alkyl halides," Nature Communications, Nature, vol. 7(1), pages 1-10, November.
    6. Muliang Zhang & Jin Xie & Chengjian Zhu, 2018. "A general deoxygenation approach for synthesis of ketones from aromatic carboxylic acids and alkenes," Nature Communications, Nature, vol. 9(1), pages 1-10, December.
    7. Rehanguli Ruzi & Kai Liu & Chengjian Zhu & Jin Xie, 2020. "Upgrading ketone synthesis direct from carboxylic acids and organohalides," Nature Communications, Nature, vol. 11(1), pages 1-9, December.
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