Faster initiation in the Friedel-Crafts reaction of benzyl fluorides using trifluoroacetic acid as activator

Rémy Hemelaere; Pier Alexandre Champagne; Justine Desroches; Jean François Paquin

doi:10.1016/j.jfluchem.2016.08.003

Faster initiation in the Friedel-Crafts reaction of benzyl fluorides using trifluoroacetic acid as activator

Rémy Hemelaere, Pier Alexandre Champagne, Justine Desroches, Jean François Paquin

Research output: Contribution to journal › Article › peer-review

31 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	1-6
Number of pages	6
Journal	Journal of Fluorine Chemistry
Volume	190
DOIs	https://doi.org/10.1016/j.jfluchem.2016.08.003
State	Published - 2016
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Environmental Chemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

Keywords

Benzyl fluorides
C-F bond activation
Friedel-Crafts alkylation
Hydrogen-bonding

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10.1016/j.jfluchem.2016.08.003

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title = "Faster initiation in the Friedel-Crafts reaction of benzyl fluorides using trifluoroacetic acid as activator",

abstract = "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 Br{\o}nsted acidity. The improved reaction conditions were applied to a set of substrates, demonstrating how they could improve yields and reliability of this transformation.",

keywords = "Benzyl fluorides, C-F bond activation, Friedel-Crafts alkylation, Hydrogen-bonding",

author = "R{\'e}my Hemelaere and Champagne, \{Pier Alexandre\} and Justine Desroches and Paquin, \{Jean Fran{\c c}ois\}",

note = "Publisher Copyright: {\textcopyright} 2016 Elsevier B.V.",

year = "2016",

doi = "10.1016/j.jfluchem.2016.08.003",

language = "English (US)",

volume = "190",

pages = "1--6",

journal = "Journal of Fluorine Chemistry",

issn = "0022-1139",

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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

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

UR - https://www.scopus.com/pages/publications/84982202474

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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 -

Faster initiation in the Friedel-Crafts reaction of benzyl fluorides using trifluoroacetic acid as activator

Abstract

All Science Journal Classification (ASJC) codes

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