Journal
SYNLETT
Volume -, Issue 6, Pages 991-993Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-2005-864813
Keywords
organocatalysis; Selectfluor; electrophilic fluorination; aldehydes; ketones
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The first organocatalytic direct alpha-fluorination of aldehydes and ketones employing Selectfluor {1-chloromethyl-4-fluoro- 1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)} as the fluorine source is reported. (S)-Proline and related derivatives act as organocatalysts to give the corresponding alpha-fluoroaldehydes and alpha-fluoroketones in moderate to good yields (47-78%). The asymmetric inductions are still low (ee <= 36%).
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