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Iron(II)-Catalyzed Benzylic Fluorination

Steven Bloom, Cody Ross Pitts, Ryan Woltornist, Andrew Griswold, Maxwell Gargiulo Holl and Thomas Lectka*

*Department of Chemistry, New Chemistry Building, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218, United States, Email: lectkajhu.edu

S. Bloom C. R. Pitts, R. Woltornist, A. Griswold, M. G. Holl, T. Lectka, Org. Lett., 2013, 15, 1722-1724.

DOI: 10.1021/ol400424s (free Supporting Information)


Abstract

A mild C-F functionalization of benzylic sp3 C-H bonds allows the synthesis of monofluorinated benzylic substrates in the presence of commercially available iron(II) acetylacetonate and Selectfluor in very good yields and selectivity. A convenient route to β-fluorinated products of 3-aryl ketones provides a synthetic equivalent to the difficult to accomplish conjugate addition of fluoride to α,β-unsaturated ketones.

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Key Words

benzyl fluorides, Selectfluor


ID: J54-Y2013-0970