Issue 8, 2015

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
23 Dec 2014
Accepted
07 Jan 2015
First published
16 Jan 2015

Org. Biomol. Chem., 2015,13, 2243-2246

Author version available

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

J. Desroches, P. A. Champagne, Y. Benhassine and J. Paquin, Org. Biomol. Chem., 2015, 13, 2243 DOI: 10.1039/C4OB02655A

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