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Temperature-Controlled Mechanochemistry for the Nickel-Catalyzed Suzuki-Miyaura-Type Coupling of Aryl Sulfamates via Ball Milling and Twin-Screw Extrusion



Bolt, Robert RA;

Raby-Buck, Sarah;

Ingram, Katherine;

Leitch, Jamie A;

Browne, Duncan L;

(2022)

Temperature-Controlled Mechanochemistry for the Nickel-Catalyzed Suzuki-Miyaura-Type Coupling of Aryl Sulfamates via Ball Milling and Twin-Screw Extrusion.

Angewandte Chemie International Edition


10.1002/anie.202210508.

(In press).

[thumbnail of Angew Chem Int Ed2022BoltTemperatureControlled Mechanochemistry for the NickelCatalyzed SuzukiMiyauraType.pdf]


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Angew Chem Int Ed2022BoltTemperatureControlled Mechanochemistry for the NickelCatalyzed SuzukiMiyauraType.pdf
– Accepted Version

Access restricted to UCL open access staff until 10 September 2023.

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Abstract

The use of temperature-controlled mechanochemistry to enable the mechanochemical nickel-catalyzed Suzuki-Miyaura coupling is herein described. Transitioning from a capricious room-temperature protocol, through to a heated, PID-controlled programmable jar heater manifold was required to deliver an efficient method for the coupling of aryl sulfamates (derived from ubiquitous phenols) and aryl boronic acid species. Furthermore, this process is conducted using a base-metal nickel catalyst, in the absence of bulk solvent, and in the absence of air/moisture sensitive reaction set-ups. This methodology is showcased through translation to large-scale twin-screw extrusion methodology enabling 200-fold scale increase, producing decagram quantities of C-C coupled material.

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