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Cu(I)-catalysed chemo-, regio-, and stereoselective radical 1,2-carboalkynylation with two different terminal alkynes

Author

Listed:
  • Jun-Qian Bian

    (Southern University of Science and Technology
    Southern University of Science and Technology)

  • Li Qin

    (Southern University of Science and Technology)

  • Li-Wen Fan

    (Southern University of Science and Technology)

  • Jiajia Fu

    (Southern University of Science and Technology)

  • Yong-Feng Cheng

    (Southern University of Science and Technology)

  • Yu-Feng Zhang

    (Southern University of Science and Technology)

  • Qiao Song

    (Southern University of Science and Technology)

  • Peng-Fei Wang

    (Southern University of Science and Technology)

  • Zhong-Liang Li

    (Great Bay University)

  • Qiang-Shuai Gu

    (Southern University of Science and Technology)

  • Peng Yu

    (Eastern Institute for Advanced Study Eastern Institute of Technology)

  • Jun-Bin Tang

    (Southern University of Science and Technology
    Southern University of Science and Technology
    Eastern Institute for Advanced Study Eastern Institute of Technology)

  • Xin-Yuan Liu

    (Southern University of Science and Technology
    Southern University of Science and Technology)

Abstract

Transition-metal-catalysed asymmetric multicomponent reactions with two similar substrates often suffer from the lack of strategies to control the chemo-, regio-, and stereoselectivity of these substrates due to the close similarity in the chemical structures and properties of each reagent. Here, we describe a Cu(I)-catalysed asymmetric radical 1,2-carboalkynylation of two different terminal alkynes and alkyl halides with high chemo-, regio-, and stereoselectivity by using sterically bulky chiral tridentate anionic N,N,P-ligands and modulating alkynes with different electronic properties to circumvent above-mentioned challenges. This method features good substrate scope, high functional group tolerance of two different terminal alkynes, and diverse alkyl halides, providing universal access to a series of useful axially chiral 1,3-enyne building blocks.

Suggested Citation

  • Jun-Qian Bian & Li Qin & Li-Wen Fan & Jiajia Fu & Yong-Feng Cheng & Yu-Feng Zhang & Qiao Song & Peng-Fei Wang & Zhong-Liang Li & Qiang-Shuai Gu & Peng Yu & Jun-Bin Tang & Xin-Yuan Liu, 2025. "Cu(I)-catalysed chemo-, regio-, and stereoselective radical 1,2-carboalkynylation with two different terminal alkynes," Nature Communications, Nature, vol. 16(1), pages 1-12, December.
    • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-60012-z
    DOI: 10.1038/s41467-025-60012-z
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    References listed on IDEAS

    as
    1. 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.
    2. Mattia Silvi & Paolo Melchiorre, 2018. "Enhancing the potential of enantioselective organocatalysis with light," Nature, Nature, vol. 554(7690), pages 41-49, February.
    3. Sheng-Cai Zheng & San Wu & Qinghai Zhou & Lung Wa Chung & Liu Ye & Bin Tan, 2017. "Erratum: Organocatalytic atroposelective synthesis of axially chiral styrenes," Nature Communications, Nature, vol. 8(1), pages 1-1, December.
    4. Jia-Lei Yan & Rakesh Maiti & Shi-Chao Ren & Weiyi Tian & Tingting Li & Jun Xu & Bivas Mondal & Zhichao Jin & Yonggui Robin Chi, 2022. "Carbene-catalyzed atroposelective synthesis of axially chiral styrenes," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    5. Fengyuan Guo & Siqiang Fang & Jiajia He & Zhishan Su & Tianli Wang, 2023. "Enantioselective organocatalytic synthesis of axially chiral aldehyde-containing styrenes via SNAr reaction-guided dynamic kinetic resolution," Nature Communications, Nature, vol. 14(1), pages 1-11, December.
    6. Sheng-Cai Zheng & San Wu & Qinghai Zhou & Lung Wa Chung & Liu Ye & Bin Tan, 2017. "Organocatalytic atroposelective synthesis of axially chiral styrenes," Nature Communications, Nature, vol. 8(1), pages 1-9, August.
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