Friedel–Crafts Reaction of Benzyl Fluorides: Selective Activation of CF Bonds as Enabled by Hydrogen Bonding1. (10th October 2014)

• Record Type: Journal Article
• Authors: Champagne, Pier Alexandre; Benhassine, Yasmine; Desroches, Justine; Paquin, Jean‐François
• Is Part Of: Angewandte Chemie. Volume 126:Number 50(2014)
• Page Start: 14055
• Page End: 14059
• Publication Date: 2014-10-10
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201406088
• Languages: English
• ISSNs: 0044-8249

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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.</p> </abstract>