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The first organocatalytic direct α-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 α-fluoroaldehydes and a-fluoroketones in moderate to good yields (47-78%). The asymmetric inductions are still low (ee ≤ 36%).
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Enders et al. (2005) studied this question.
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