HUSY zeolite-promoted reactions of trifluoromethylated propargyl alcohols with arenes: synthesis of CF3-indenes and DFT study of intermediate carbocations

Selbi K. Nursahedova; Aleksey V. Zerov; Irina A. Boyarskaya; Elena V. Grinenko; Valentine G. Nenajdenko; Aleksander V. Vasilyev

doi:10.1039/C8OB02887G

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HUSY zeolite-promoted reactions of trifluoromethylated propargyl alcohols with arenes: synthesis of CF₃-indenes and DFT study of intermediate carbocations†

Selbi K. Nursahedova,^a Aleksey V. Zerov,^b Irina A. Boyarskaya,^b Elena V. Grinenko,^a Valentine G. Nenajdenko

*^c and Aleksander V. Vasilyev

*^ab

Author affiliations

* Corresponding authors

^a Department of Chemistry, Saint Petersburg State Forest Technical University, Institutsky per., 5, Saint Petersburg, Russia
E-mail: aleksvasil@mail.ru, a.vasilyev@spbu.ru

^b Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, Saint Petersburg, Russia

^c Department of Chemistry, Lomonosov Moscow State University, Vorobievy Gory, 1, Moscow, Russia
E-mail: nenajdenko@org.chem.msu.ru

Abstract

The reaction of CF₃-propargyl alcohols [ArC [triple bond, length as m-dash] CCH(OH)CF₃] with arenes under the action of acidic HUSY zeolite CBV-720 was investigated. It was found that the reaction at 100 °C for 1 h gave rise to 3-aryl-1-CF₃-indenes in up to 83% yield. Electronic characteristics of the reaction key intermediates, mesomeric CF₃-propargyl-allenyl cations [ArC [triple bond, length as m-dash] C−HC⁺(CF₃) ↔ ArC⁺ [double bond, length as m-dash] CCH(CF₃)], were studied by DFT calculations. A plausible cationic reaction mechanism is discussed.

This article is part of the themed collections: Synthetic methodology in OBC and Mechanistic, computational & physical organic chemistry in OBC

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Article information

DOI: https://doi.org/10.1039/C8OB02887G
Article type: Paper
Submitted: 19 Nov 2018
Accepted: 10 Jan 2019
First published: 10 Jan 2019

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Org. Biomol. Chem., 2019,17, 1215-1224

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HUSY zeolite-promoted reactions of trifluoromethylated propargyl alcohols with arenes: synthesis of CF₃-indenes and DFT study of intermediate carbocations

S. K. Nursahedova, A. V. Zerov, I. A. Boyarskaya, E. V. Grinenko, V. G. Nenajdenko and A. V. Vasilyev, Org. Biomol. Chem., 2019, 17, 1215 DOI: 10.1039/C8OB02887G

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Organic & Biomolecular Chemistry