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Divergent ring-opening coupling between cyclopropanols and alkynes under cobalt catalysis† †Electronic supplementary information (ESI) available. CCDC 1826866. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8sc02074d
| Content Provider | Semantic Scholar |
|---|---|
| Author | Yang, Junfeng Shen, Yixiao Lim, Yang Jie Yoshikai, Naohiko |
| Copyright Year | 2018 |
| Abstract | Cobalt-diphosphine catalysts promote ring-opening coupling reactions between cyclopropanols and unactivated internal alkynes, affording either β-alkenyl ketones or multisubstituted cyclopentenol derivatives in good yields with good to excellent regioselectivities. The chemoselectivity between these β-alkenylation and [3 + 2] annulation reactions, which likely share a cobalt homoenolate as a key catalytic intermediate, is exquisitely controlled by the reaction conditions, with the solvent being a major controlling factor. The reactions are proposed to involve ring opening of cobalt cyclopropoxide into homoenolate, migratory insertion of the alkyne into the Co-C bond, and protodemetalation or intramolecular carbonyl addition of the resulting alkenylcobalt species. The feasibility of these reaction steps was supported by DFT calculations. |
| Starting Page | 6928 |
| Ending Page | 6934 |
| Page Count | 7 |
| File Format | PDF HTM / HTML |
| DOI | 10.1039/c8sc02074d |
| Alternate Webpage(s) | http://www.rsc.org/suppdata/c8/sc/c8sc02074d/c8sc02074d1.pdf |
| PubMed reference number | 30210767 |
| Alternate Webpage(s) | https://doi.org/10.1039/c8sc02074d |
| Journal | Medline |
| Volume Number | 9 |
| Journal | Chemical science |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
