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Chemo-, regio- and stereoselective access to polysubstituted 1,3-dienes via Nickel-catalyzed four-component reactions

Author

Listed:
  • Shanglin Chen

    (College of Chemistry at Fuzhou University)

  • Ya-Nan Wang

    (Chongqing University)

  • Jinhui Xie

    (College of Chemistry at Fuzhou University)

  • Wangyang Li

    (College of Chemistry at Fuzhou University)

  • Mingxing Ye

    (College of Chemistry at Fuzhou University)

  • Xingxing Ma

    (College of Chemistry at Fuzhou University)

  • Kai Yang

    (College of Chemistry at Fuzhou University)

  • Shijun Li

    (Zhengzhou University)

  • Yu Lan

    (Chongqing University
    Zhengzhou University)

  • Qiuling Song

    (College of Chemistry at Fuzhou University
    Henan Normal University)

Abstract

1,2-Difunctionalization of alkynes offers a straightforward approach to access polysubstituted alkenes. However, simultaneous multi-component cascade transformations including difunctionalization of two alkynes with both syn- and anti-selectivity in one catalyst system is undeveloped and proves to be a significant challenge. Herein, we report a Nickel-catalyzed four-component reaction to access polysubstituted 1,3-dienes using two terminal alkynes, aryl boroxines, and perfluoroalkyl iodides, wherein the reaction forms three new C-C bonds in a single vessel and serve as a modular strategy to access polysubstituted 1,3-dienes with excellent chemoselectivity, good regioselectivity and exclusive stereoselectivity. Control experiments reveal the plausible reaction mechanism and DFT calculations explain the cause for the formation of this unusual four-component reaction. Furthermore, we successfully incorporate two biologically active units into 1,2,3,4-tetrasubstituted 1,3-dienes, which greatly increases the diversity of molecular scaffolds and brings more potential values to medicinal chemistry, the synthetic utility of our protocol is further demonstrated by the late-stage transformations.

Suggested Citation

  • Shanglin Chen & Ya-Nan Wang & Jinhui Xie & Wangyang Li & Mingxing Ye & Xingxing Ma & Kai Yang & Shijun Li & Yu Lan & Qiuling Song, 2024. "Chemo-, regio- and stereoselective access to polysubstituted 1,3-dienes via Nickel-catalyzed four-component reactions," Nature Communications, Nature, vol. 15(1), pages 1-14, December.
  • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-49870-1
    DOI: 10.1038/s41467-024-49870-1
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    References listed on IDEAS

    as
    1. Xian Zhao & Hai-Yong Tu & Lei Guo & Shengqing Zhu & Feng-Ling Qing & Lingling Chu, 2018. "Intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay," Nature Communications, Nature, vol. 9(1), pages 1-7, December.
    2. Shengnan Jin & Jinxia Li & Kang Liu & Wei-Yi Ding & Shuai Wang & Xiujuan Huang & Xue Li & Peiyuan Yu & Qiuling Song, 2022. "Enantioselective Cu-catalyzed double hydroboration of alkynes to access chiral gem-diborylalkanes," Nature Communications, Nature, vol. 13(1), pages 1-12, December.
    3. Yufeng Sun & Jun Guo & Xuzhong Shen & Zhan Lu, 2022. "Ligand relay catalysis for cobalt-catalyzed sequential hydrosilylation and hydrohydrazidation of terminal alkynes," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    4. Lei Guo & Fan Song & Shengqing Zhu & Huan Li & Lingling Chu, 2018. "syn-Selective alkylarylation of terminal alkynes via the combination of photoredox and nickel catalysis," Nature Communications, Nature, vol. 9(1), pages 1-8, December.
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