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Issue 39, 2017
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Synthesis of γ-keto sulfones by copper-catalyzed oxidative sulfonylation of tertiary cyclopropanols

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Abstract

Tertiary cyclopropanols undergo ring-opening oxidative sulfonylation to afford γ-keto sulfones when reacting with sulfinate salts in the presence of a copper(II) acetate catalyst and an oxidant (tert-butyl hydroperoxide or atmospheric oxygen). Various fluoroalkyl, aryl and alkyl sulfinate salts are successfully employed as sulfonylation reagents, affording the corresponding sulfones in up to 94% yields. The experimental protocol is mild and tolerates a number of functionalities in the cyclopropanol substrate. The reaction proceeds via a one-pot oxidation–Michael addition mechanism and can serve as a useful addition to the existing methods for the preparation of γ-keto sulfones based on the sulfa-Michael reaction.

Graphical abstract: Synthesis of γ-keto sulfones by copper-catalyzed oxidative sulfonylation of tertiary cyclopropanols

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Publication details

The article was received on 02 Jul 2017, accepted on 12 Sep 2017 and first published on 12 Sep 2017


Article type: Paper
DOI: 10.1039/C7OB01605K
Citation: Org. Biomol. Chem., 2017,15, 8334-8340
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    Synthesis of γ-keto sulfones by copper-catalyzed oxidative sulfonylation of tertiary cyclopropanols

    Y. A. Konik, G. Z. Elek, S. Kaabel, I. Järving, M. Lopp and D. G. Kananovich, Org. Biomol. Chem., 2017, 15, 8334
    DOI: 10.1039/C7OB01605K

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