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Bifunctional iron-catalyzed alkyne Z-selective hydroalkylation and tandem Z-E inversion via radical molding and flipping

Author

Listed:
  • Yongqiang Zhang

    (Dalian University of Technology)

  • Dongmin Fu

    (Zhengzhou University)

  • Ziyang Chen

    (Dalian University of Technology)

  • Rongqi Cui

    (Dalian University of Technology)

  • Wenlong He

    (Dalian University of Technology)

  • Hongyao Wang

    (Dalian University of Technology)

  • Jiajin Chen

    (Dalian University of Technology)

  • Yufei Chen

    (Dalian University of Technology)

  • Shi-Jun Li

    (Zhengzhou University)

  • Yu Lan

    (Zhengzhou University
    Chongqing University)

  • Chunying Duan

    (Nanjing University)

  • Yunhe Jin

    (Dalian University of Technology)

Abstract

The challenging synthesis of thermodynamic-unfavored cis-olefins through catalytic cross-coupling reactions requires the synergistic interaction of substrate-activating units and configuration-regulating catalysts. Successfully hitting these two birds with one stone, we herein develop a convenient photoredox access to Z-alkenes from alkynes and light alkanes with a bifunctional iron-catalyzed system possessing both C(sp3)−H activation and configuration-controlling abilities. The protocol exhibits 100% atom utilization, mild conditions, a broad substrate scope, and compatibility with multitudinous functional groups. The detailed reaction mechanism and the origin of geometry regulation are well investigated by experimental and computational studies. Progressively, a catalytic amount of diaryl disulfides is introduced for consecutive photoinduced Z−E isomerization via reversible radical addition and flipping. Big steric hindrance substituents assembled on the disulfide emerge necessity for suppressing double-bond migration. This tandem strategy paves a promising way for stereoselective alkene construction and will bring significant inspiration for the development of transition metal photocatalysis.

Suggested Citation

  • Yongqiang Zhang & Dongmin Fu & Ziyang Chen & Rongqi Cui & Wenlong He & Hongyao Wang & Jiajin Chen & Yufei Chen & Shi-Jun Li & Yu Lan & Chunying Duan & Yunhe Jin, 2024. "Bifunctional iron-catalyzed alkyne Z-selective hydroalkylation and tandem Z-E inversion via radical molding and flipping," Nature Communications, Nature, vol. 15(1), pages 1-13, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-53021-x
    DOI: 10.1038/s41467-024-53021-x
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    References listed on IDEAS

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    1. Heng Rao & Luciana C. Schmidt & Julien Bonin & Marc Robert, 2017. "Visible-light-driven methane formation from CO2 with a molecular iron catalyst," Nature, Nature, vol. 548(7665), pages 74-77, August.
    2. Ping-Fu Zhong & Jia-Lin Tu & Yating Zhao & Nan Zhong & Chao Yang & Lin Guo & Wujiong Xia, 2023. "Photoelectrochemical oxidative C(sp3)−H borylation of unactivated hydrocarbons," Nature Communications, Nature, vol. 14(1), pages 1-11, December.
    3. Ming Joo Koh & R. Kashif M. Khan & Sebastian Torker & Miao Yu & Malte S. Mikus & Amir H. Hoveyda, 2015. "High-value alcohols and higher-oxidation-state compounds by catalytic Z-selective cross-metathesis," Nature, Nature, vol. 517(7533), pages 181-186, January.
    4. Geun Seok Lee & Daeun Kim & Soon Hyeok Hong, 2021. "Pd-catalyzed formal Mizoroki–Heck coupling of unactivated alkyl chlorides," Nature Communications, Nature, vol. 12(1), pages 1-12, December.
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