Reaction of Benzopinacol with Non-ionic Bases: Reversing the Pinacol Coupling
The reaction of benzopinacol with the non-ionic bases butyllithium and phosphazene P4 leads to the formation of the corresponding ketyl radical anions, which have been characterized by EPR/ENDOR spectroscopy. This conversion has a high efficiency. Such a reversed pinacol reaction can be used for a c...
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| Veröffentlicht in: | Organic letters 2013-09, Vol.15 (18), p.4627-4629 |
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| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
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| Zusammenfassung: | The reaction of benzopinacol with the non-ionic bases butyllithium and phosphazene P4 leads to the formation of the corresponding ketyl radical anions, which have been characterized by EPR/ENDOR spectroscopy. This conversion has a high efficiency. Such a reversed pinacol reaction can be used for a controlled release of ketyl radicals. Moreover, the nature of the base has a marked effect on the association of the ketyl radical anion and the counterions. This illustrates the importance of ion pairing for reductive coupling. |
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| ISSN: | 1523-7060 1523-7052 |
| DOI: | 10.1021/ol402253s |