Solid-state Suzuki-Miyaura cross-coupling reactions: olefin-accelerated C-C coupling using mechanochemistry

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...

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Veröffentlicht in:Chemical science (Cambridge) 2019-09, Vol.1 (35), p.822-821
Hauptverfasser: Seo, Tamae, Ishiyama, Tatsuo, Kubota, Koji, Ito, Hajime
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Sprache:eng
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Zusammenfassung: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. The first general solid-state Suzuki-Miyaura cross-coupling reactions using mechanochemistry has been developed.
ISSN:2041-6520
2041-6539
DOI:10.1039/c9sc02185j