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Related Experiment Videos

Visible-Light-Induced Tandem Nickel-Catalyzed Heck Cyclization/Self-Promoted [2+2] Intermolecular Cycloaddition.

Xiaogang Tong1, Linlin Ren1, Yonggong Wang1

  • 1Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Key Laboratory of Research and Development of Natural Products, School of Pharmacy, Yunnan University, Kunming 650500, China.

Organic Letters
|March 12, 2025
PubMed
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Visible-light nickel catalysis enables new chemical reactions by accelerating anti-β-hydride elimination in Heck cyclization. A novel tandem reaction involving [2+2] photocycloaddition was also discovered without extra photocatalysts.

Area of Science:

  • Organic Chemistry
  • Photocatalysis
  • Organometallic Chemistry

Background:

  • Visible-light photocatalysis offers a sustainable approach to chemical synthesis.
  • Nickel complexes are increasingly utilized as photocatalysts, primarily through Ni(II) homolysis or alkyl halide activation.
  • Existing methods for Heck cyclization and [2+2] photocycloaddition often require specific photocatalysts or harsh conditions.

Purpose of the Study:

  • To explore novel applications of photoexcited nickel species in organic transformations.
  • To investigate the mechanism by which nickel photocatalysts influence Heck cyclization.
  • To discover new tandem reactions facilitated by visible-light photocatalysis.

Main Methods:

  • Utilizing visible-light irradiation in conjunction with nickel catalysts.

Related Experiment Videos

  • Investigating the acceleration of anti-β-hydride elimination in Heck cyclization reactions.
  • Characterizing a tandem reaction involving intermolecular [2+2] photocycloaddition.

    • Main Results:

    • Photoexcited nickel species were found to accelerate the anti-β-hydride elimination step in Heck cyclization.
    • A novel tandem reaction was developed, combining Heck cyclization with a substrate self-promoted intermolecular [2+2] photocycloaddition.
    • This tandem reaction proceeded efficiently without the need for additional photocatalysts.

    Conclusions:

    • Visible-light nickel catalysis provides a powerful platform for promoting challenging organic transformations.
    • The acceleration of anti-β-hydride elimination by photoexcited nickel opens new avenues in Heck cyclization.
    • The discovered tandem reaction highlights the potential for developing highly efficient, catalyst-free processes under visible light.