title: Friedel-Crafts reaction of benzyl fluorides: selective activation of C-F bonds as enabled by hydrogen bonding.
abstract: A Friedel-Crafts benzylation of arenes with benzyl fluorides has been developed. The reaction produces 1,1-diaryl alkanes in good yield under mild conditions without the need for a transition metal or a strong Lewis acid. A mechanism involving activation of the C-F bond through hydrogen bonding is proposed. This mode of activation enables the selective reaction of benzylic C-F bonds in the presence of other benzylic leaving groups.
authors.affiliation: Canada Research Chair in Organic and Medicinal Chemistry, CCVC, PROTEO, Département de chimie, Université Laval, 1045 Avenue de la Médecine, Pavillon Alexandre-Vachon, Québec, Québec, G1V 0A6 (Canada).
authors.forename: Pier Alexandre
authors.initials: PA
authors.lastname: Champagne
authors.forename: Yasmine
authors.initials: Y
authors.lastname: Benhassine
authors.forename: Justine
authors.initials: J
authors.lastname: Desroches
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Paquin
keywords: CF activation; Friedel-Crafts reaction; arenes; benzyl fluorides; hydrogen bonds