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Friedel–Crafts Reaction of Benzyl Fluorides: Selective Activation of CF Bonds as Enabled by Hydrogen Bonding
Author(s) -
Champagne Pier Alexandre,
Benhassine Yasmine,
Desroches Justine,
Paquin JeanFrançois
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201406088
Subject(s) - friedel–crafts reaction , chemistry , hydrogen bond , lewis acids and bases , yield (engineering) , polymer chemistry , metal , medicinal chemistry , catalysis , organic chemistry , photochemistry , molecule , materials science , metallurgy
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 CF bond through hydrogen bonding is proposed. This mode of activation enables the selective reaction of benzylic CF bonds in the presence of other benzylic leaving groups.