Bis(2-methoxyethyl)aminosulfur trifluoride, (CH3OCH2CH2)2NSF3 (Deoxo-Fluor reagent), is a new
deoxofluorinating agent that is much more thermally stable than DAST (C2H5)2NSF3 and its
congeners. It is effective for the conversion of alcohols to alkyl fluorides, aldehydes/ketones to the
corresponding gem-difluorides, and carboxylic acids to the trifluoromethyl derivatives with, in some
cases, superior performance compared to DAST. The enhanced stability is rationalized on the basis
of conformational rigidity imposed by a coordination of the alkoxy groups with the electron-deficient
sulfur atom of the trifluoride.
The new "N-F"-type electrophilic reagent family of l-alkyl-4-fluoro-l,4-diazabicyclo[2.2.2]octane salts80 (derived from elemental fluorine (F2) and l-alkyl-l,4-diazabicyclo[2.2.2]octane salts) has been found to be very effective for the fluorination of a wide variety of organic substrates. These include steroidal enol acetates and silyl enol ethers, phenyl-substituted olefins, sulfides bearing -H atoms, certain carbanions, and mildly activated aromatic compounds. The products were obtained with good yields and regioselectivity under very mild reaction conditions.
Bis(2-methoxyethyl)aminosulfur trifluoride (Deoxo-Fluor™) is effective for the conversion of alcohols to alkyl fluorides, aldehydes/ketones to the corresponding gemdifluorides and also for the transformation of carboxylic acids to their trifluoromethyl derivatives; it is a less thermally sensitive, broader-spectrum alternative to the traditional dialkylaminosulfur trifluoride (DAST) deoxofluorination reagents.
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
A variety of thiocarbonyl derivatives (thioketone, thioester, thioamide, dithioester, and dithiocarbamate) were converted to the corresponding gem-difluorides in excellent yields on reaction with the fluorinating agent, bis(2-methoxyethyl)aminosulfur trifluoride, in the presence of SbCl(3).
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.