94404-29-2Relevant articles and documents
Nickel-Catalyzed Decarbonylative Synthesis of Fluoroalkyl Thioethers
Brigham, Conor E.,Malapit, Christian A.,Lalloo, Naish,Sanford, Melanie S.
, p. 8315 - 8320 (2020/08/28)
This report describes the development of a nickel-catalyzed decarbonylative reaction for the synthesis of fluoroalkyl thioethers (RFSR) from the corresponding thioesters. Readily available, inexpensive, and stable fluoroalkyl carboxylic acids (RFCO2H) serve as the fluoroalkyl (RF) source in this transformation. Stoichiometric organometallic studies reveal that RF-S bond-forming reductive elimination is a challenging step in the catalytic cycle. This led to the identification of diphenylphosphinoferrocene as the optimal ligand for this transformation. Ultimately, this method was applied to the construction of diverse fluoroalkyl thioethers (RFSR), with R = both aryl and alkyl.
Bis(2-methoxyethyl)aminosulfur trifluoride: A new broad-spectrum deoxofluorinating agent with enhanced thermal stability
Lal, Gauri S.,Pez, Guido P.,Pesaresi, Reno J.,Prozonic, Frank M.,Cheng, Hansong
, p. 7048 - 7054 (2007/10/03)
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.
Fluoro-Pummerer rearrangement under oxidative desulfurization fluorination conditions. Facile synthesis of oligofluoroalkyl sulfides
Furuta, Satoru,Kuroboshi, Manabu,Hiyama, Tamejiro
, p. 8243 - 8246 (2007/10/02)
Upon treatment with n-Bu4NH2F3 and 1,3-dibromo-5,5-dimethylhydantoin, various organic sulfides were readily fluorinated to give α-fluoro sulfides. When (HF)9-Py was used as the fluorinating agent, normal oxidative desulfurization fluorination occurred depending on the structure of the substrates.