Issue 35, 2019

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

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.

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

Supplementary files

Article information

Article type
Edge Article
Submitted
06 5月 2019
Accepted
21 7月 2019
First published
22 7月 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 8202-8210

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

T. Seo, T. Ishiyama, K. Kubota and H. Ito, Chem. Sci., 2019, 10, 8202 DOI: 10.1039/C9SC02185J

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