Friedel-crafts reaction of benzyl fluorides: Selective activation of C-f bonds as enabled by hydrogen bonding

Pier Alexandre Champagne; Yasmine Benhassine; Justine Desroches; Jean François Paquin

doi:10.1002/anie.201406088

Friedel-crafts reaction of benzyl fluorides: Selective activation of C-f bonds as enabled by hydrogen bonding

Pier Alexandre Champagne, Yasmine Benhassine, Justine Desroches, Jean François Paquin

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

210 Scopus citations

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.

Original language	English (US)
Pages (from-to)	13835-13839
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	53
Issue number	50
DOIs	https://doi.org/10.1002/anie.201406088
State	Published - Oct 10 2014
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry

Keywords

Arenes
Benzyl fluorides
C-F activation
Friedel-Crafts reaction
Hydrogen bonds

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10.1002/anie.201406088

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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.",

keywords = "Arenes, Benzyl fluorides, C-F activation, Friedel-Crafts reaction, Hydrogen bonds",

author = "Champagne, \{Pier Alexandre\} and Yasmine Benhassine and Justine Desroches and Paquin, \{Jean Fran{\c c}ois\}",

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year = "2014",

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doi = "10.1002/anie.201406088",

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pages = "13835--13839",

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T1 - Friedel-crafts reaction of benzyl fluorides

T2 - Selective activation of C-f bonds as enabled by hydrogen bonding

AU - Champagne, Pier Alexandre

AU - Benhassine, Yasmine

AU - Desroches, Justine

AU - Paquin, Jean François

PY - 2014/10/10

Y1 - 2014/10/10

N2 - 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.

AB - 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.

KW - Arenes

KW - Benzyl fluorides

KW - C-F activation

KW - Friedel-Crafts reaction

KW - Hydrogen bonds

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DO - 10.1002/anie.201406088

M3 - Article

AN - SCOPUS:84919361231

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VL - 53

SP - 13835

EP - 13839

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 50

ER -

Friedel-crafts reaction of benzyl fluorides: Selective activation of C-f bonds as enabled by hydrogen bonding

Abstract

All Science Journal Classification (ASJC) codes

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