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Two-step conversion of carboxylic esters into distally fluorinated ketones via ring cleavage of cyclopropanol intermediates: application of sulfinate salts as fluoroalkylating reagents

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Abstract

Tertiary cyclopropanols easily available from carboxylic esters have been used in the synthesis of distally fluorinated ketones. Cyclopropane ring cleavage reactions in methanol with aqueous tert-butyl hydroperoxide in the presence of a copper(II) acetate catalyst and sodium triflinate (Langlois reagent) afford β-trifluoromethyl ketones in 16–74% isolated yields. Sodium triflinate serves as a precursor of reactive trifluoromethyl copper species, enabling ring-opening trifluoromethylation, as evidenced by mechanistic studies. We also demonstrate here that other sulfinate salts, such as sodium 1,1-difluoroethanesulfinate, sodium 2-(4-bromophenyl)-1,1-difluoroethanesulfinate and sodium 1-(trifluoromethyl)cyclopropanesulfinate, can be used as fluoroalkylation reagents, resulting in the corresponding fluorinated ketones.

Graphical abstract: Two-step conversion of carboxylic esters into distally fluorinated ketones via ring cleavage of cyclopropanol intermediates: application of sulfinate salts as fluoroalkylating reagents

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Publication details

The article was received on 20 Mar 2017, accepted on 04 May 2017 and first published on 08 May 2017


Article type: Paper
DOI: 10.1039/C7OB00680B
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Two-step conversion of carboxylic esters into distally fluorinated ketones via ring cleavage of cyclopropanol intermediates: application of sulfinate salts as fluoroalkylating reagents

    Y. A. Konik, M. Kudrjashova, N. Konrad, S. Kaabel, I. Järving, M. Lopp and D. G. Kananovich, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB00680B

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