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Solid-state Suzuki–Miyaura cross-coupling reactions: olefin-accelerated C–C coupling using mechanochemistry† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c9sc02185j
| Content Provider | Semantic Scholar |
|---|---|
| Author | Seo, Tamae Ishiyama, Tatsuo Kubota, Koji Ito, Hajime |
| Copyright Year | 2019 |
| 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. |
| Starting Page | 8202 |
| Ending Page | 8210 |
| Page Count | 9 |
| File Format | PDF HTM / HTML |
| DOI | 10.1039/c9sc02185j |
| PubMed reference number | 31857886 |
| Journal | Medline |
| Volume Number | 10 |
| Alternate Webpage(s) | http://www.rsc.org/suppdata/c9/sc/c9sc02185j/c9sc02185j1.pdf |
| Alternate Webpage(s) | https://ftp.ncbi.nlm.nih.gov/pub/pmc/oa_pdf/87/ed/SC-010-C9SC02185J.PMC6836942.pdf |
| Alternate Webpage(s) | https://doi.org/10.1039/c9sc02185j |
| Journal | Chemical science |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |