Olefin–Borane “van der Waals Complexes”: Intermediates in Frustrated Lewis Pair Addition Reactions
The nature of the borane–olefin interactions that take place prior to frustrated Lewis pair addition reactions has been probed employing a Lewis acidic borane tethered to a vinyl group through an alkyl chain. 1H{19F} HOESY spectral data obtained at −50 °C demonstrated the spatial proximity of the bo...
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| Veröffentlicht in: | Journal of the American Chemical Society 2011-08, Vol.133 (32), p.12448-12450 |
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| Hauptverfasser: | , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
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| Zusammenfassung: | The nature of the borane–olefin interactions that take place prior to frustrated Lewis pair addition reactions has been probed employing a Lewis acidic borane tethered to a vinyl group through an alkyl chain. 1H{19F} HOESY spectral data obtained at −50 °C demonstrated the spatial proximity of the boryl and vinyl groups and computational data support the initial formation of a van der Waals borane–olefin complex. Such species serve as intermediates undergoing facile addition reactions with phosphine bases to afford cyclic zwitterionic products. |
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| ISSN: | 0002-7863 1520-5126 |
| DOI: | 10.1021/ja205598k |