Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 15, Issue 39, Pages 8334-8340Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7ob01605k
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Funding
- European Union's Seventh Framework Program for research, technological development and demonstration [621364]
- Centre of Excellence in Molecular Cell Engineering [2014-2020.4.01.15-0013]
- Estonian Ministry of Education and Research [IUT19-32]
- Tallinn University of Technology [B58]
- Tallinn University of Technology
- [IUT19-9]
- [PUT692]
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Tertiary cyclopropanols undergo ring-opening oxidative sulfonylation to afford gamma-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 gamma-keto sulfones based on the sulfa-Michael reaction.
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