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Iron/phosphine-catalyzed reductive cross-coupling to construct quaternary carbon centers

Author

Listed:
  • Qiao Zhang

    (Nankai University
    Haihe Laboratory of Sustainable Chemical Transformations)

  • Xiang-Yu Liu

    (Nankai University)

  • Yu-Yu Li

    (Nankai University)

  • Ming-Yao Huang

    (Nankai University)

  • Shou-Fei Zhu

    (Nankai University
    Haihe Laboratory of Sustainable Chemical Transformations)

Abstract

Transition metal-catalyzed C–C reductive coupling reactions avoid the direct use of sensitive metal reagents, representing a practical approach for constructing the skeletons of organic compounds. However, such reactions face significant challenges in constructing quaternary carbon centers. Herein, we report an example of iron-catalyzed reductive cross-coupling reaction of tertiary alkyl halides with allyl halides by using phosphine ligands. A directing strategy is developed for diverse reductive couplings of 3o C(sp3) with 1o C(sp3) and even 2o C(sp3). The directing effect of the carbonyl of amides and esters facilitates the iron catalyst in overcoming the substantial steric hindrance and numerous competing side reactions, allowing the reaction to proceed smoothly. The current study develops a directing strategy for highly steric reductive coupling reactions, and offers new insights into the efficient construction of complex C(sp3)–C(sp3) bonds using iron catalysts modified with phosphine ligands.

Suggested Citation

  • Qiao Zhang & Xiang-Yu Liu & Yu-Yu Li & Ming-Yao Huang & Shou-Fei Zhu, 2025. "Iron/phosphine-catalyzed reductive cross-coupling to construct quaternary carbon centers," Nature Communications, Nature, vol. 16(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-64781-5
    DOI: 10.1038/s41467-025-64781-5
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    References listed on IDEAS

    as
    1. Kyle W. Quasdorf & Larry E. Overman, 2014. "Catalytic enantioselective synthesis of quaternary carbon stereocentres," Nature, Nature, vol. 516(7530), pages 181-191, December.
    2. Ji-Jun Chen & Jia-Heng Fang & Xuan-Yi Du & Jia-Yong Zhang & Jun-Qian Bian & Fu-Li Wang & Cheng Luan & Wei-Long Liu & Ji-Ren Liu & Xiao-Yang Dong & Zhong-Liang Li & Qiang-Shuai Gu & Zhe Dong & Xin-Yuan, 2023. "Enantioconvergent Cu-catalysed N-alkylation of aliphatic amines," Nature, Nature, vol. 618(7964), pages 294-300, June.
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