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Open AccessArticle

TfOH-Promoted Reaction of 2,4-Diaryl-1,1,1-Trifluorobut-3-yn-2-oles with Arenes: Synthesis of 1,3-Diaryl-1-CF3-Indenes and Versatility of the Reaction Mechanisms

1
Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, Saint Petersburg 199034, Russia
2
Department of Crystallography, Institute of Earth Sciences, Saint Petersburg State University, Universitetskaya nab., 7/9, Saint Petersburg 199034, Russia
3
Center for X-ray Diffraction Studies, Research park, St. Petersburg State University, Universitetskiy pr. 26, Saint Petersburg, Petrodvoretz198504, Russia
4
Department of Chemistry, Saint Petersburg State Forest Technical University, Institutsky per., 5, Saint Petersburg 194021, Russia
*
Author to whom correspondence should be addressed.
Academic Editor: Igor V. Alabugin
Molecules 2018, 23(12), 3079; https://doi.org/10.3390/molecules23123079
Received: 5 November 2018 / Revised: 16 November 2018 / Accepted: 17 November 2018 / Published: 25 November 2018
(This article belongs to the Special Issue Alkynes: From Reaction Design to Applications in Organic Synthesis)
The TfOH-mediated reactions of 2,4-diaryl-1,1,1-trifluorobut-3-yn-2-oles (CF3-substituted diaryl propargyl alcohols) with arenes in CH2Cl2 afford 1,3-diaryl-1-CF3-indenes in yields up to 84%. This new process for synthesis of such CF3-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 CF3-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. View Full-Text
Keywords: trifluoromethyl propargyl alcohols; trifluoromethyl indenes; triflic acid; propargyl cations; cationic reaction mechanism trifluoromethyl propargyl alcohols; trifluoromethyl indenes; triflic acid; propargyl cations; cationic reaction mechanism
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Zerov, A.V.; Kazakova, A.N.; Boyarskaya, I.A.; Panikorovskii, T.L.; Suslonov, V.V.; Khoroshilova, O.V.; Vasilyev, A.V. TfOH-Promoted Reaction of 2,4-Diaryl-1,1,1-Trifluorobut-3-yn-2-oles with Arenes: Synthesis of 1,3-Diaryl-1-CF3-Indenes and Versatility of the Reaction Mechanisms. Molecules 2018, 23, 3079.

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