Iron(II)-Catalyzed Benzylic Fluorination
2013
Bloom, Steve | Pitts, Cody Ross | Woltornist, Ryan | Griswold, Andrew | Holl, Maxwell Gargiulo | Lectka, Thomas
Direct C–F functionalization of benzylic sp³ C–H bonds is a synthetic challenge that has yet to be propitiously overcome. A mild, one-pot synthesis of monofluorinated benzylic substrates is reported with commercially available iron(II) acetylacetonate and Selectfluor in good to excellent yields and selectivity. A convenient route to β-fluorinated products of 3-aryl ketones is also highlighted, providing a synthetic equivalent to the difficult to accomplish conjugate addition of fluoride to α,β-unsaturated ketones.
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