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Palladium catalyzed radical relay for the oxidative cross-coupling of quinolines

Author

Listed:
  • Xiaorui Zhao

    (Shanghai Normal University
    Taishan University)

  • Xiaojuan Zhu

    (Shanghai Normal University)

  • Kang Wang

    (Shanghai Normal University)

  • Junqian Lv

    (Shanghai Normal University)

  • Shangjun Chen

    (Shanghai Normal University)

  • Guohua Yao

    (Shanghai Normal University)

  • Junyu Lang

    (Shanghai Tech University)

  • Fei Lv

    (Shanghai Normal University)

  • Yinghui Pu

    (Chinese Academy of Sciences)

  • Ruoou Yang

    (Huazhong University of Science and Technology)

  • Bingsen Zhang

    (Chinese Academy of Sciences)

  • Zheng Jiang

    (Chinese Academy of Sciences)

  • Ying Wan

    (Shanghai Normal University)

Abstract

Traditional approaches for transition-metal catalyzed oxidative cross-coupling reactions rely on sp2-hybridized starting materials, such as aryl halides, and more specifically, homogeneous catalysts. We report a heterogeneous Pd-catalyzed radical relay method for the conversion of a heteroarene C(sp3)–H bond into ethers. Pd nanoparticles are supported on an ordered mesoporous composite which, when compared with microporous activated carbons, greatly increases the Pd d charge because of their strong interaction with N-doped anatase nanocrystals. Mechanistic studies provide evidence that electron-deficient Pd with Pd–O/N coordinations efficiently catalyzes the radical relay reaction to release diffusible methoxyl radicals, and highlight the difference between this surface reaction and C–H oxidation mediated by homogeneous catalysts that operate with cyclopalladated intermediates. The reactions proceed efficiently with a turn-over frequency of 84 h−1 and high selectivity toward ethers of >99%. Negligible Pd leaching and activity loss are observed after 7 catalytic runs.

Suggested Citation

  • Xiaorui Zhao & Xiaojuan Zhu & Kang Wang & Junqian Lv & Shangjun Chen & Guohua Yao & Junyu Lang & Fei Lv & Yinghui Pu & Ruoou Yang & Bingsen Zhang & Zheng Jiang & Ying Wan, 2022. "Palladium catalyzed radical relay for the oxidative cross-coupling of quinolines," Nature Communications, Nature, vol. 13(1), pages 1-11, December.
  • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-31967-0
    DOI: 10.1038/s41467-022-31967-0
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    References listed on IDEAS

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    1. Xiaojuan Zhu & Qishui Guo & Yafei Sun & Shangjun Chen & Jian-Qiang Wang & Mengmeng Wu & Wenzhao Fu & Yanqiang Tang & Xuezhi Duan & De Chen & Ying Wan, 2019. "Optimising surface d charge of AuPd nanoalloy catalysts for enhanced catalytic activity," Nature Communications, Nature, vol. 10(1), pages 1-11, December.
    2. Zhe Zhuang & Jin-Quan Yu, 2020. "Author Correction: Lactonization as a general route to β-C(sp3)–H functionalization," Nature, Nature, vol. 586(7828), pages 11-11, October.
    3. Zhe Zhuang & Jin-Quan Yu, 2020. "Lactonization as a general route to β-C(sp3)–H functionalization," Nature, Nature, vol. 577(7792), pages 656-659, January.
    4. Huang Zhou & Yafei Zhao & Jie Xu & Haoran Sun & Zhijun Li & Wei Liu & Tongwei Yuan & Wei Liu & Xiaoqian Wang & Weng-Chon Cheong & Zhiyuan Wang & Xin Wang & Chao Zhao & Yancai Yao & Wenyu Wang & Fangya, 2020. "Recover the activity of sintered supported catalysts by nitrogen-doped carbon atomization," Nature Communications, Nature, vol. 11(1), pages 1-9, December.
    5. Zhe Chang & Jialin Huang & Si Wang & Geshuyi Chen & Heng Zhao & Rui Wang & Depeng Zhao, 2021. "Copper catalyzed late-stage C(sp3)-H functionalization of nitrogen heterocycles," Nature Communications, Nature, vol. 12(1), pages 1-11, December.
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