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

Yulia A. Konik, Gábor Zoltán Elek, Sandra Kaabel, Ivar Järving, Margus Lopp, Dzmitry G. Kananovich*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

27 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)8334-8340
Number of pages7
JournalORGANIC AND BIOMOLECULAR CHEMISTRY
Volume15
Issue number39
DOIs
Publication statusPublished - 2017
MoE publication typeA1 Journal article-refereed

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