Journal
TETRAHEDRON
Volume 74, Issue 27, Pages 3507-3511Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2018.04.083
Keywords
Cyclopropenium cation; Fluorination; Phase transfer catalysis; Hydrogen bond; Benzylic fluorination
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Funding
- Natural Sciences and Engineering Research Council of Canada (NSERC) [201404410]
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The application of cyclopropenium ion as a phase transfer catalyst for benzylic fluorination in high yields is reported. Integral to the mechanisms of these fluorination reactions was the role of in situ derived cyclopropenium fluoride complexes, the existence of which was supported by H-1, F-19 NMR and UV-Vis spectroscopy. Density functional theory calculations were applied to gain insight into the mechanism of these reactions. (C) 2018 Elsevier Ltd. All rights reserved.
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