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TfOH-Promoted Reaction of 2,4-Diaryl-1,1,1-Trifluorobut-3-yn-2-oles with Arenes: Synthesis of 1,3-Diaryl-1-CF<sub>3</sub>-Indenes and Versatility of the Reaction Mechanisms

By Aleksey V. Zerov, Anna N. Kazakova, Irina A. Boyarskaya, Taras L. Panikorovskii, Vitalii V. Suslonov, Olesya V. Khoroshilova and Aleksander V. Vasilyev

Abstract

The TfOH-mediated reactions of 2,4-diaryl-1,1,1-trifluorobut-3-yn-2-oles (CF<sub>3</sub>-substituted diaryl propargyl alcohols) with arenes in CH<sub>2</sub>Cl<sub>2</sub> afford 1,3-diaryl-1-CF<sub>3</sub>-indenes in yields up to 84%. This new process for synthesis of such CF<sub>3</sub>-indenes is complete at room temperature within one hour. The synthetic potential, scope, and limitations of this reaction were illustrated by more than 70 examples. The proposed reaction mechanism invokes the formation of highly reactive CF<sub>3</sub>-propargyl cation intermediates that can be trapped at the two mesomeric positions by the intermolecular nucleophilic attack of an arene partner with a subsequent intramolecular ring closure

Topics: trifluoromethyl propargyl alcohols, trifluoromethyl indenes, triflic acid, propargyl cations, cationic reaction mechanism, Organic chemistry, QD241-441
Publisher: MDPI AG
Year: 2018
DOI identifier: 10.3390/molecules23123079
OAI identifier: oai:doaj.org/article:3a0727588e3c4835be5dc121dc79b842
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