Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 35, Pages 7071-7075Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201101307
Keywords
Lewis acids; Cycloaddition; Kinetics; NMR spectroscopy
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Funding
- Deutsche Forschungsgemeinschaft
- Millennium Pharmaceuticals, Inc., Cambridge, USA
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The Lewis acidity of various silyl triflates was quantified by utilizing [D5]pyridine as a 2H NMR spectroscopy probe. The chemical shifts of the 2H NMR signals for pyridinesilyl adducts are reported. The rate constants of silyl triflate catalyzed DielsAlder reactions were determined by using UV/Vis spectroscopy. A correlation of the magnitude of the 2H NMR chemical shifts with the rate constants for most silyl triflates investigated was observed, but Me3SiOTf exhibits a surprisingly large deviation. Control experiments indicate that proton catalysis of the DielsAlder reaction can be excluded.
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