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Chemoselective carbene insertion into the N−H bonds of NH3·H2O

Author

Listed:
  • Zhaohong Liu

    (Northeast Normal University)

  • Yong Yang

    (Northeast Normal University)

  • Qingmin Song

    (Northeast Normal University)

  • Linxuan Li

    (Northeast Normal University)

  • Giuseppe Zanoni

    (University of Pavia)

  • Shaopeng Liu

    (Northeast Normal University)

  • Meng Xiang

    (Northeast Normal University)

  • Edward A. Anderson

    (University of Oxford)

  • Xihe Bi

    (Northeast Normal University
    Nankai University)

Abstract

The conversion of inexpensive aqueous ammonia (NH3·H2O) into value-added primary amines by N−H insertion persists as a longstanding challenge in chemistry because of the tendency of Lewis basic ammonia (NH3) to bind and inhibit metal catalysts. Herein, we report a chemoselective carbene N−H insertion of NH3·H2O using a TpBr3Ag-catalyzed two-phase system. Coordination by a homoscorpionate TpBr3 ligand renders silver compatible with NH3 and H2O and enables the generation of electrophilic silver carbene. Water promotes subsequent [1,2]-proton shift to generate N−H insertion products with high chemoselectivity. The result of the reaction is the coupling of an inorganic nitrogen source with either diazo compounds or N-triftosylhydrazones to produce useful primary amines. Further investigations elucidate the reaction mechanism and the origin of chemoselectivity.

Suggested Citation

  • Zhaohong Liu & Yong Yang & Qingmin Song & Linxuan Li & Giuseppe Zanoni & Shaopeng Liu & Meng Xiang & Edward A. Anderson & Xihe Bi, 2022. "Chemoselective carbene insertion into the N−H bonds of NH3·H2O," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-35394-z
    DOI: 10.1038/s41467-022-35394-z
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    References listed on IDEAS

    as
    1. Yuya Ashida & Kazuya Arashiba & Kazunari Nakajima & Yoshiaki Nishibayashi, 2019. "Molybdenum-catalysed ammonia production with samarium diiodide and alcohols or water," Nature, Nature, vol. 568(7753), pages 536-540, April.
    2. Zhaohong Liu & Hongwei Wang & Paramasivam Sivaguru & Steven P. Nolan & Qingmin Song & Weijie Yu & Xinyu Jiang & Edward A. Anderson & Xihe Bi, 2022. "Silver-catalyzed site-selective C(sp3)−H benzylation of ethers with N-triftosylhydrazones," Nature Communications, Nature, vol. 13(1), pages 1-12, December.
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