Solid-state cross-coupling reactions of insoluble aryl halides under polymer-assisted grinding conditions
Koji Kubota1,2, Tamae Seo1, Hajime Ito1,2
1Division of Applied Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo, Hokkaido, Japan. kbt@eng.hokudai.ac.jp.
Abstract:
In this study, polymer-assisted grinding (POLAG), a ball-milling technique based on the use of polymer additives, was applied to mechanochemical solid-state Suzuki-Miyaura cross-coupling reactions of insoluble aryl halides. We found that the efficiency of this challenging solid-state cross-coupling was improved by the addition of polytetrafluoroethylene (PTFE) as a POLAG additive under high-temperature ball-milling conditions. Our results suggest that POLAG is a promising approach for controlling the reactivity of insoluble substrates that are barely reactive under conventional solution-based conditions.
Related Concept Videos
Nucleophilic Aromatic Substitution: Elimination–Addition
Acid Halides to Alcohols: Grignard Reaction
Grignard reagents are a source of carbanions and function as nucleophiles. The mechanism begins with the nucleophilic attack by the carbanion at the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs,...
Preparation and Reactions of Sulfides
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Cycloaddition Reactions: MO Requirements for Thermal Activation
SN2 Reaction: Transition State
When the nucleophile approaches the electrophilic carbon with its lone pairs, the halide acts as a leaving group and moves away with the electron-pair bonded to the carbon. Dotted partial bonds represent the bonds being formed or broken...
![Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F51444.jpg&w=3840&q=50)

![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)