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Robert R A Bolt1, Sarah E Raby-Buck1, Katharine Ingram2

  • 1Department of Pharmaceutical and Biological Chemistry, University College London (UCL), School of Pharmacy, 29-39 Brunswick Square, Bloomsbury, London, WC1N 1AX, UK.

Angewandte Chemie (International Ed. in English)
|September 9, 2022
PubMed
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A new nickel-catalyzed Suzuki-Miyaura coupling reaction uses mechanochemistry and a programmable jar heater. This solvent-free, air-stable method was successfully scaled up for practical applications.

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Mechanochemistry

Background:

  • Suzuki-Miyaura coupling is a vital carbon-carbon bond-forming reaction.
  • Developing base-metal catalysts for Suzuki-Miyaura coupling is crucial for sustainable chemistry.
  • Mechanochemistry offers solvent-free reaction conditions, aligning with green chemistry principles.

Purpose of the Study:

  • To report a novel nickel-catalyzed Suzuki-Miyaura-type coupling of aryl sulfamates and boronic acid derivatives.
  • To utilize temperature-controlled mechanochemistry for this transformation.
  • To develop a scalable and practical protocol.

Main Methods:

  • Employing nickel catalysis for the Suzuki-Miyaura-type coupling.
  • Utilizing temperature-controlled mechanochemistry with a programmable PID-controlled jar heater.
Keywords:
Cross-CouplingMechanochemistryNickel CatalysisTwin-Screw Extrusion

Related Experiment Videos

  • Performing the reaction under solvent-free and all-under-air conditions.

    • Main Results:

    • Successful Suzuki-Miyaura-type coupling of aryl sulfamates and boronic acid derivatives was achieved.
    • The reaction proceeded efficiently under mechanochemical conditions.
    • The protocol was scaled up 200-fold using twin-screw extrusion, yielding decagram quantities.

    Conclusions:

    • A novel, efficient, and scalable nickel-catalyzed Suzuki-Miyaura coupling protocol has been developed.
    • Temperature-controlled mechanochemistry provides a viable route for solvent-free cross-coupling reactions.
    • The developed method offers a practical approach for synthesizing valuable compounds on a larger scale.