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Intermolecular diastereoselective annulation of azaarenes into fused N-heterocycles by Ru(II) reductive catalysis

Author

Listed:
  • He Zhao

    (South China University of Technology)

  • Yang Wu

    (South China University of Technology)

  • Chenggang Ci

    (Qiannan Normal University for Nationalities)

  • Zhenda Tan

    (South China University of Technology)

  • Jian Yang

    (South China University of Technology)

  • Huanfeng Jiang

    (South China University of Technology)

  • Pierre H. Dixneuf

    (University of Rennes, ISCR, UMR CNRS 6226)

  • Min Zhang

    (South China University of Technology)

Abstract

Derivatization of azaarenes can create molecules of biological importance, but reductive functionalization of weakly reactive azaarenes remains a challenge. Here the authors show a dearomative, diastereoselective annulation of azaarenes, via ruthenium(II) reductive catalysis, proceeding with excellent selectivity, mild conditions, and broad substrate and functional group compatibility. Mechanistic studies reveal that the products are formed via hydride transfer-initiated β-aminomethylation and α-arylation of the pyridyl core in the azaarenes, and that paraformaldehyde serves as both the C1-building block and reductant precursor, and the use of Mg(OMe)2 base plays a critical role in determining the reaction chemo-selectivity by lowering the hydrogen transfer rate. The present work opens a door to further develop valuable reductive functionalization of unsaturated systems by taking profit of formaldehyde-endowed two functions.

Suggested Citation

  • He Zhao & Yang Wu & Chenggang Ci & Zhenda Tan & Jian Yang & Huanfeng Jiang & Pierre H. Dixneuf & Min Zhang, 2022. "Intermolecular diastereoselective annulation of azaarenes into fused N-heterocycles by Ru(II) reductive catalysis," Nature Communications, Nature, vol. 13(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-29985-z
    DOI: 10.1038/s41467-022-29985-z
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    References listed on IDEAS

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    1. Wen-Jun Zhou & Zhe-Hao Wang & Li-Li Liao & Yuan-Xu Jiang & Ke-Gong Cao & Tao Ju & Yiwen Li & Guang-Mei Cao & Da-Gang Yu, 2020. "Reductive dearomative arylcarboxylation of indoles with CO2 via visible-light photoredox catalysis," Nature Communications, Nature, vol. 11(1), pages 1-9, December.
    2. Saravanakumar Elangovan & Jacob Neumann & Jean-Baptiste Sortais & Kathrin Junge & Christophe Darcel & Matthias Beller, 2016. "Efficient and selective N-alkylation of amines with alcohols catalysed by manganese pincer complexes," Nature Communications, Nature, vol. 7(1), pages 1-8, November.
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