An oxidative carbon-carbon bond-forming reaction proceeds via an isolable iminium ion
The mechanism of our previously reported DDQ-mediated oxidative C-C bond-forming reaction is investigated. We are able to trap and characterize an iminium ion intermediate with X-ray crystallography, elemental analysis, and solid-state NMR spectroscopy; to our knowledge this is the first time this p...
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| Hauptverfasser: | , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Deutsch |
| Veröffentlicht: |
7. Februar 2011
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| In: |
Pure and applied chemistry
Year: 2011, Jahrgang: 83, Heft: 3, Pages: 655-665 |
| ISSN: | 1365-3075 |
| DOI: | 10.1351/PAC-CON-11-01-01 |
| Online-Zugang: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1351/PAC-CON-11-01-01 Verlag, lizenzpflichtig, Volltext: https://www.degruyterbrill.com/document/doi/10.1351/PAC-CON-11-01-01/html 
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| Verfasserangaben: | Althea S.-K. Tsang, Paul Jensen, James M. Hook, A. Stephen K. Hashmi, and Matthew H. Todd |
| Zusammenfassung: | The mechanism of our previously reported DDQ-mediated oxidative C-C bond-forming reaction is investigated. We are able to trap and characterize an iminium ion intermediate with X-ray crystallography, elemental analysis, and solid-state NMR spectroscopy; to our knowledge this is the first time this putative intermediate ion has been directly observed in such cross-dehydrogenative couplings (CDCs). The intermediate can be reacted with a range of nucleo-philes, including a malonate that is not amenable to a one-pot reaction protocol. |
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| Beschreibung: | Gesehen am 17.11.2022 |
| Beschreibung: | Online Resource |
| ISSN: | 1365-3075 |
| DOI: | 10.1351/PAC-CON-11-01-01 |