TY - JOUR
T1 - Faster initiation in the Friedel-Crafts reaction of benzyl fluorides using trifluoroacetic acid as activator
AU - Hemelaere, Rémy
AU - Champagne, Pier Alexandre
AU - Desroches, Justine
AU - Paquin, Jean François
N1 - Funding Information:
This work was supported by the Natural Sciences and Engineering Research Council of Canada, the Fonds de recherche du Québec – Nature et technologies, and the Université Laval.
Publisher Copyright:
© 2016 Elsevier B.V.
PY - 2016
Y1 - 2016
N2 - We report that the addition of a catalytic amount of trifluoroacetic acid (TFA) shortens the induction period associated with the 1,1,1,3,3,3-hexafluoroisopropoanol (HFIP)-promoted Friedel-Crafts reaction of benzylic fluorides. This faster initiation is due to TFA's strong hydrogen-bond donation capability, not its Brønsted acidity. The improved reaction conditions were applied to a set of substrates, demonstrating how they could improve yields and reliability of this transformation.
AB - We report that the addition of a catalytic amount of trifluoroacetic acid (TFA) shortens the induction period associated with the 1,1,1,3,3,3-hexafluoroisopropoanol (HFIP)-promoted Friedel-Crafts reaction of benzylic fluorides. This faster initiation is due to TFA's strong hydrogen-bond donation capability, not its Brønsted acidity. The improved reaction conditions were applied to a set of substrates, demonstrating how they could improve yields and reliability of this transformation.
KW - Benzyl fluorides
KW - C-F bond activation
KW - Friedel-Crafts alkylation
KW - Hydrogen-bonding
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U2 - 10.1016/j.jfluchem.2016.08.003
DO - 10.1016/j.jfluchem.2016.08.003
M3 - Article
AN - SCOPUS:84982202474
SN - 0022-1139
VL - 190
SP - 1
EP - 6
JO - Journal of Fluorine Chemistry
JF - Journal of Fluorine Chemistry
ER -