TfOH-promoted transformation of TMS-ethers of diarylsubstituted CF3-allyl alcohols with arenes into CF3-indanes

Aleksey V. Zerov; Anastasia A. Bulova; Olesya V. Khoroshilova; Aleksander V. Vasilyev

doi:10.1039/C9QO00822E

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TfOH-promoted transformation of TMS-ethers of diarylsubstituted CF₃-allyl alcohols with arenes into CF₃-indanes†

Aleksey V. Zerov,^a Anastasia A. Bulova,^a Olesya V. Khoroshilova^b and Aleksander V. Vasilyev

*^ac

Author affiliations

* Corresponding authors

^a Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, Saint Petersburg, Russia
E-mail: aleksvasil@mail.ru, a.vasilyev@spbu.ru

^b Research Center for X-ray Diffraction Studies, Research Park, St. Petersburg State University, Universitetskiy pr. 26, Saint Petersburg, Russia

^c Department of Chemistry, Saint Petersburg State Forest Technical University, Institutsky per., 5, Saint Petersburg, Russia

Abstract

The reaction of TMS-ethers of 2,4-diaryl-1,1,1-trifluorobut-3-en-2-ols with arenes in TfOH at room temperature for 5 min results in the formation of trans-/cis-1,3-diaryl-1-trifluoromethyl indanes in good yields (up to 99%). The predominant or exclusive formation of indanes with a trans-configuration of 1,3-diaryl groups has been observed. The reaction proceeds through an intermediate formation of the corresponding mesomeric CF₃-allyl cations. A plausible reaction mechanism is discussed.

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Article information

DOI: https://doi.org/10.1039/C9QO00822E
Article type: Research Article
Submitted: 27 Jun 2019
Accepted: 04 Aug 2019
First published: 05 Aug 2019

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Org. Chem. Front., 2019,6, 3264-3268

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TfOH-promoted transformation of TMS-ethers of diarylsubstituted CF₃-allyl alcohols with arenes into CF₃-indanes

A. V. Zerov, A. A. Bulova, O. V. Khoroshilova and A. V. Vasilyev, Org. Chem. Front., 2019, 6, 3264 DOI: 10.1039/C9QO00822E

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