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Rhodium-catalyzed selective direct arylation of phosphines with aryl bromides

Author

Listed:
  • Dingyi Wang

    (Nanjing University)

  • Mingjie Li

    (Nanjing University)

  • Chengdong Shuang

    (Nanjing University)

  • Yong Liang

    (Nanjing University)

  • Yue Zhao

    (Nanjing University)

  • Minyan Wang

    (Nanjing University)

  • Zhuangzhi Shi

    (Nanjing University
    Henan Normal University)

Abstract

The widespread use of phosphine ligand libraries is frequently hampered by the challenges associated with their modular preparation. Here, we report a protocol that appends arenes to arylphosphines to access a series of biaryl monophosphines via rhodium-catalyzed P(III)-directed ortho C–H activation, enabling unprecedented one-fold, two-fold, and three-fold direct arylation. Our experimental and theoretical findings reveal a mechanism involving oxidative addition of aryl bromides to the Rh catalyst, further ortho C–H metalation via a four-membered cyclometalated ring. Given the ready availability of substrates, our approach opens the door to developing more general methods for the construction of phosphine ligands.

Suggested Citation

  • Dingyi Wang & Mingjie Li & Chengdong Shuang & Yong Liang & Yue Zhao & Minyan Wang & Zhuangzhi Shi, 2022. "Rhodium-catalyzed selective direct arylation of phosphines with aryl bromides," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-30697-7
    DOI: 10.1038/s41467-022-30697-7
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    References listed on IDEAS

    as
    1. Paulina Seweryn & Lan Bich Van & Morten Kjeldgaard & Christopher J. Russo & Lori A. Passmore & Bjarne Hove-Jensen & Bjarne Jochimsen & Ditlev E. Brodersen, 2015. "Structural insights into the bacterial carbon–phosphorus lyase machinery," Nature, Nature, vol. 525(7567), pages 68-72, September.
    2. Dingyi Wang & Ben Dong & Yandong Wang & Jiasheng Qian & Jinjun Zhu & Yue Zhao & Zhuangzhi Shi, 2019. "Rhodium-catalysed direct hydroarylation of alkenes and alkynes with phosphines through phosphorous-assisted C−H activation," Nature Communications, Nature, vol. 10(1), pages 1-10, December.
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