Work

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

Year: 2019

Type: article

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.

Source: Chemical Science

DOI: 10.1039/c9sc02185j

Authors: Tamae Seo, Tatsuo Ishiyama, Koji Kubota, Hajime Ito

Institutions: Hokkaido University, Institute for Chemical Reaction Design and Discovery

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: Ministry of Education, Culture, Sports, Science and Technology, Japan Society for the Promotion of Science

Awards: Asymmetric Borylation with Chiral Dense Reaction Space, Concise synthesis of nanographene by solid-state cross-coupling reaction, G1912957829, G3407872060, Highly regioselective carbon-hydrogen bond direct boronation using substrate functional groups and metal catalyst ligands