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Trends in Organic Chemistry   Volumes    Volume 20 
Efficient access to unsymmetrical triarylmethanes by regioselective Friedel-Crafts hydroxyalkylation
Maité Sylla Iyarreta Veitía, Céline Rampal, Clotilde Ferroud
Pages: 1 - 13
Number of pages: 13
Trends in Organic Chemistry
Volume 20 

Copyright © 2019 Research Trends. All rights reserved

Friedel-Crafts alkylation is one of the most important methods used in organic chemistry to create carbon-carbon bonds. The traditional conditions using alkyl halides activated by a Lewis or Brønsted acid have been widely described in the literature. Nevertheless, the Friedel-Crafts reaction using aldehydes or ketones as substrates, known as hydroxyalkylation, has been poorly described. The development of regioselective Friedel-Crafts conditions is a challenge in organic synthesis. The growing interest in developing “metal and solvent-free” reactions justifies the special attention that the Brønsted acids have received as an alternative to toxic and precious metals. During the last few years, triarylmethanes have attracted considerable attention due to their applications in fine, medicinal and industrial chemistry. They have been used as protecting groups, dyes or photochromic agents. They also exhibit interesting biological properties including anti-tumor and antioxidant activities. Different methods of preparation of symmetrical triarylmethanes have been described in the literature; nonetheless, the synthesis of unsymmetrical ones has been very little explored. In this work we describe an efficient regioselective method to prepare unsymmetrical triarylmethanes, via a Friedel-Crafts hydroxyalkylation catalyzed by Brønsted acids using pyridylarylcarbinols as alkylating agents. The method described here is consistent with the principles of green chemistry and has significant advantages, such as the use of an inexpensive catalyst and mild conditions. This regioselective method offers good yields, shorter reaction times and a possible extension to various substrates.
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