In situ activation of benzyl alcohols with XtalFluor-E: Formation of 1,1-diarylmethanes and 1,1,1-triarylmethanes through Friedel-Crafts benzylation

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

doi:10.1039/c4ob02655a

In situ activation of benzyl alcohols with XtalFluor-E: Formation of 1,1-diarylmethanes and 1,1,1-triarylmethanes through Friedel-Crafts benzylation

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

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

34 Scopus citations

Abstract

The Friedel-Crafts benzylation of arenes using benzyl alcohols activated in situ with XtalFluor-E is described. A wide range of 1,1-diarylmethanes and 1,1,1-triarylmethanes were prepared under experimentally simple and mild conditions, without the need for a transition metal or a strong Lewis acid. Notably, the reactivity observed demonstrates the potential of XtalFluor-E to induce C-OH bond ionization and S_N1 reactivity of benzylic alcohols.

Original language	English (US)
Pages (from-to)	2243-2246
Number of pages	4
Journal	Organic and Biomolecular Chemistry
Volume	13
Issue number	8
DOIs	https://doi.org/10.1039/c4ob02655a
State	Published - 2015
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "In situ activation of benzyl alcohols with XtalFluor-E: Formation of 1,1-diarylmethanes and 1,1,1-triarylmethanes through Friedel-Crafts benzylation",

abstract = "The Friedel-Crafts benzylation of arenes using benzyl alcohols activated in situ with XtalFluor-E is described. A wide range of 1,1-diarylmethanes and 1,1,1-triarylmethanes were prepared under experimentally simple and mild conditions, without the need for a transition metal or a strong Lewis acid. Notably, the reactivity observed demonstrates the potential of XtalFluor-E to induce C-OH bond ionization and SN1 reactivity of benzylic alcohols.",

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

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2015.",

year = "2015",

doi = "10.1039/c4ob02655a",

language = "English (US)",

volume = "13",

pages = "2243--2246",

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T2 - Formation of 1,1-diarylmethanes and 1,1,1-triarylmethanes through Friedel-Crafts benzylation

AU - Desroches, Justine

AU - Champagne, Pier Alexandre

AU - Benhassine, Yasmine

AU - Paquin, Jean François

N1 - Publisher Copyright: © The Royal Society of Chemistry 2015.

PY - 2015

Y1 - 2015

N2 - The Friedel-Crafts benzylation of arenes using benzyl alcohols activated in situ with XtalFluor-E is described. A wide range of 1,1-diarylmethanes and 1,1,1-triarylmethanes were prepared under experimentally simple and mild conditions, without the need for a transition metal or a strong Lewis acid. Notably, the reactivity observed demonstrates the potential of XtalFluor-E to induce C-OH bond ionization and SN1 reactivity of benzylic alcohols.

AB - The Friedel-Crafts benzylation of arenes using benzyl alcohols activated in situ with XtalFluor-E is described. A wide range of 1,1-diarylmethanes and 1,1,1-triarylmethanes were prepared under experimentally simple and mild conditions, without the need for a transition metal or a strong Lewis acid. Notably, the reactivity observed demonstrates the potential of XtalFluor-E to induce C-OH bond ionization and SN1 reactivity of benzylic alcohols.

UR - https://www.scopus.com/pages/publications/84922762568

UR - https://www.scopus.com/pages/publications/84922762568#tab=citedBy

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EP - 2246

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 8

ER -

In situ activation of benzyl alcohols with XtalFluor-E: Formation of 1,1-diarylmethanes and 1,1,1-triarylmethanes through Friedel-Crafts benzylation

Abstract

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