Issue 39, 2015
From the journal:

Chemical Communications

Simple access to β-trifluoromethyl-substituted ketones via copper-catalyzed ring-opening trifluoromethylation of substituted cyclopropanols†‡

Dzmitry G. Kananovich,*a   Yulia A. Konik,b   Dzmitry M. Zubrytski,b   Ivar Järvinga  and  Margus Lopp*a  

* Corresponding authors

a Department of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia
E-mail: dzmitry.kananovich@ttu.ee, margus.lopp@ttu.ee

b Department of Organic Chemistry, Belarusian State University, Leningradskaya 14, Minsk, Belarus

Abstract

Tertiary cyclopropanols react rapidly with Togni reagent in methanol at room temperature in the presence of catalytic amounts (3 mol%) of CuCl affording β-trifluoromethyl ketones in 65–73% isolated yields. Ring opening in 1,2-dialkylsubstituted cyclopropanols gives a mixture of isomeric β-trifluoromethyl ketones in about 50% combined yield.

Graphical abstract: Simple access to β-trifluoromethyl-substituted ketones via copper-catalyzed ring-opening trifluoromethylation of substituted cyclopropanols

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Article information

DOI
https://doi.org/10.1039/C5CC02386F
Article type
Communication
Submitted
22 Mar 2015
Accepted
07 Apr 2015
First published
09 Apr 2015

Chem. Commun., 2015,51, 8349-8352

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Simple access to β-trifluoromethyl-substituted ketones via copper-catalyzed ring-opening trifluoromethylation of substituted cyclopropanols

D. G. Kananovich, Y. A. Konik, D. M. Zubrytski, I. Järving and M. Lopp, Chem. Commun., 2015, 51, 8349 DOI: 10.1039/C5CC02386F

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