Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 15, Issue 21, Pages 4635-4643Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7ob00680b
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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 [IUT 19-32]
- Tallinn University of Technology [B58]
- Dora Plus program
- [IUT19-9]
- [PUT692]
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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 beta-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.
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