Issue 39, 2017

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

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

Supplementary files

Article information

Article type
Paper
Submitted
02 Jul 2017
Accepted
12 Sep 2017
First published
12 Sep 2017

Org. Biomol. Chem., 2017,15, 8334-8340

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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