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Solid-state Suzuki-Miyaura cross-coupling reactions: olefin-accelerated C-C coupling using mechanochemistry
Tamae Seo1, Tatsuo Ishiyama1, Koji Kubota1,2
1Division of Applied Chemistry and Frontier Chemistry Center , Faculty of Engineering , Hokkaido University , Sapporo , Hokkaido , Japan . Email: hajito@eng.hokudai.ac.jp ;
Abstract:
The Suzuki-Miyaura cross-coupling reaction is one of the most reliable methods for the construction of carbon-carbon bonds in solution. However, examples for the corresponding solid-state cross-coupling reactions remain scarce. Herein, we report the first broadly applicable mechanochemical protocol for a solid-state palladium-catalyzed organoboron cross-coupling reaction using an olefin additive. Compared to previous studies, the newly developed protocol shows a substantially broadened substrate scope. Our mechanistic data suggest that olefin additives might act as dispersants for the palladium-based catalyst to suppress higher aggregation of the nanoparticles, and also as stabilizer for the active monomeric Pd(0) species, thus facilitating these challenging solid-state C-C bond forming cross-coupling reactions.
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