Temperature‐Controlled Mechanochemistry for the Nickel‐Catalyzed Suzuki–Miyaura‐Type Coupling of Aryl Sulfamates via Ball Milling and Twin‐Screw Extrusion.** DOI
Robert R. A. Bolt, Sarah E. Raby‐Buck,

Katharine Ingram

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(44)

Published: Sept. 9, 2022

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 heated, PID‐controlled programmable jar heater manifold was required deliver an efficient method for aryl sulfamates (derived ubiquitous phenols) and boronic acid species. Furthermore, this process conducted using base‐metal nickel catalyst, in absence bulk solvent, air/moisture sensitive reaction set‐ups. This methodology showcased translation large‐scale twin‐screw extrusion enabling 200‐fold scale increase, producing decagram quantities C−C coupled material.

Language: Английский

Mechanochemical Grignard Reactions with Gaseous CO2 and Sodium Methyl Carbonate** DOI Creative Commons
Victoria S. Pfennig, Romina C. Villella, Julia Nikodemus

et al.

Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 61(9)

Published: Dec. 23, 2021

Abstract A one‐pot, three‐step protocol for the preparation of Grignard reagents from organobromides in a ball mill and their subsequent reactions with gaseous carbon dioxide (CO 2 ) or sodium methyl carbonate providing aryl alkyl carboxylic acids up to 82 % yield is reported. Noteworthy are short reaction times significantly reduced solvent amounts [2.0 equiv. liquid assisted grinding (LAG) conditions]. Unexpectedly, bromides methoxy substituents lead symmetric ketones as major products.

Language: Английский

Citations

63

Mechanochemical techniques for the activation and use of zero-valent metals in synthesis DOI
Andrew C. Jones, Jamie A. Leitch, Sarah E. Raby‐Buck

et al.

Nature Synthesis, Journal Year: 2022, Volume and Issue: 1(10), P. 763 - 775

Published: July 21, 2022

Language: Английский

Citations

63

Efficient access to materials-oriented aromatic alkynes via the mechanochemical Sonogashira coupling of solid aryl halides with large polycyclic conjugated systems DOI Creative Commons
Yunpeng Gao, Chi Feng,

Tamae Seo

et al.

Chemical Science, Journal Year: 2021, Volume and Issue: 13(2), P. 430 - 438

Published: Dec. 8, 2021

Using a high-temperature ball-milling technique, practical mechanochemical protocol for the Sonogashira cross-coupling of polyaromatic halides was achieved, which provides efficient access to materials-oriented aromatic alkynes.

Language: Английский

Citations

62

The Mechanochemical Synthesis and Activation of Carbon‐Richπ‐Conjugated Materials DOI Creative Commons
Mingjun Xuan, Christian Schumacher, Carsten Bolm

et al.

Advanced Science, Journal Year: 2022, Volume and Issue: 9(19)

Published: Jan. 20, 2022

Mechanochemistry uses mechanical force to break, form, and manipulate chemical bonds achieve functional transformations syntheses. Over the last years, many innovative applications of mechanochemistry have been developed. Specifically for synthesis activation carbon-rich π-conjugated materials, offers reaction pathways that either are inaccessible with other stimuli, such as light heat, or improve yields, energy consumption, substrate scope. Therefore, this review summarizes recent advances in research field combining viewpoints polymer trituration mechanochemistry. The highlighted mechanochemical include materials optical probes, force-induced release small dye molecules, polyacetylene, carbon allotropes, materials.

Language: Английский

Citations

51

Temperature‐Controlled Mechanochemistry for the Nickel‐Catalyzed Suzuki–Miyaura‐Type Coupling of Aryl Sulfamates via Ball Milling and Twin‐Screw Extrusion.** DOI
Robert R. A. Bolt, Sarah E. Raby‐Buck,

Katharine Ingram

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(44)

Published: Sept. 9, 2022

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 heated, PID‐controlled programmable jar heater manifold was required deliver an efficient method for aryl sulfamates (derived ubiquitous phenols) and boronic acid species. Furthermore, this process conducted using base‐metal nickel catalyst, in absence bulk solvent, air/moisture sensitive reaction set‐ups. This methodology showcased translation large‐scale twin‐screw extrusion enabling 200‐fold scale increase, producing decagram quantities C−C coupled material.

Language: Английский

Citations

48