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Nickel-Catalyzed Reductive Three-Component Cross-Coupling of Butadiene with Aldehydes and Alkenyl Triflates/Bromides: Access to Skipped Dienes

  • Yan Xu
    Yan Xu
    College of Chemistry and Materials Science, Sichuan Normal University, Chengdu 610068, People’s Republic of China
    More by Yan Xu
  • Tong Su
    Tong Su
    College of Chemistry and Materials Science, Sichuan Normal University, Chengdu 610068, People’s Republic of China
    More by Tong Su
  • Jie-Rui Zhang
    Jie-Rui Zhang
    College of Chemistry and Materials Science, Sichuan Normal University, Chengdu 610068, People’s Republic of China
  • Hua-Jiao Ding
    Hua-Jiao Ding
    College of Chemistry and Materials Science, Sichuan Normal University, Chengdu 610068, People’s Republic of China
  • Yuanji Gao
    Yuanji Gao
    College of Chemistry and Materials Science, Sichuan Normal University, Chengdu 610068, People’s Republic of China
    More by Yuanji Gao
  • Minghui Xu
    Minghui Xu
    College of Chemistry and Materials Science, Sichuan Normal University, Chengdu 610068, People’s Republic of China
    More by Minghui Xu
  • Peng Cao
    Peng Cao
    College of Chemistry and Materials Science, Sichuan Normal University, Chengdu 610068, People’s Republic of China
    More by Peng Cao
  • Ping Hu
    Ping Hu
    College of Chemistry and Materials Science, Sichuan Normal University, Chengdu 610068, People’s Republic of China
    More by Ping Hu
  • Bi-Qin Wang
    Bi-Qin Wang
    College of Chemistry and Materials Science, Sichuan Normal University, Chengdu 610068, People’s Republic of China
    More by Bi-Qin Wang
  • , and 
  • Bin Chen*
    Bin Chen
    College of Chemistry and Materials Science, Sichuan Normal University, Chengdu 610068, People’s Republic of China
    *E-mail: [email protected]
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Cite this: Org. Lett. 2023, 25, 17, 3136–3140
Publication Date (Web):April 26, 2023
https://doi.org/10.1021/acs.orglett.3c01036
Copyright © 2023 American Chemical Society

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Abstract

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A regio- and stereoselective nickel-catalyzed reductive three-component cross-coupling of 1,3-butadiene with aldehydes and alkenyl triflates or bromides was realized. This protocol afforded a convenient approach to the synthesis of skipped diene compounds bearing various functionals and heterocyclic groups. The utility of this reaction was also demonstrated by scale-up preparation and diverse transformations.

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The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.3c01036.

  • Experimental details and analytical data (NMR, HRMS) (PDF)

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