title: Fe(III)/NaBH4-mediated free radical hydrofluorination of unactivated alkenes.
abstract: A powerful Fe(III)/NaBH(4)-mediated free radical hydrofluorination of unactivated alkenes is disclosed using Selectfluor reagent as a source of fluorine and resulting in exclusive Markovnikov addition. In contrast to the traditional and unmanageable free radical hydrofluorination of alkenes, the Fe(III)/NaBH(4)-mediated reaction is conducted under exceptionally mild reaction conditions (0 °C, 5 min, CH(3)CN/H(2)O). The reaction can be conducted open to the air and with water as a cosolvent and demonstrates an outstanding substrate scope and functional group tolerance.
authors.affiliation: Department of Chemistry and Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
authors.forename: Timothy J
authors.initials: TJ
authors.lastname: Barker
authors.forename: Dale L
authors.initials: DL
authors.lastname: Boger
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001894:Borohydrides / Q000737:chemistry*; D002384:Catalysis; D005290:Ferric Compounds / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry*; D054879:Halogenation
chemical_list: D000475:Alkenes; D001894:Borohydrides; D005290:Ferric Compounds; D005609:Free Radicals; C025364:sodium borohydride