74185-83-4Relevant academic research and scientific papers
Selective C-F Functionalization of Unactivated Trifluoromethylarenes
Vogt, David B.,Seath, Ciaran P.,Wang, Hengbin,Jui, Nathan T.
supporting information, p. 13203 - 13211 (2019/09/03)
Fluorinated organic molecules are pervasive within the pharmaceutical and agrochemical industries due to the range of structural and physicochemical properties that fluorine imparts. Currently, the most abundant methods for the synthesis of the aryl-CF2 functionality have relied on the deoxyfluorination of ketones and aldehydes using expensive and poorly atom economical reagents. Here, we report a general method for the synthesis of aryl-CF2R and aryl-CF2H compounds through activation of the corresponding trifluoromethyl arene precursors. This strategy is enabled by an endergonic electron transfer event that provides access to arene radical anions that lie outside of the catalyst reduction potential. Fragmentation of these reactive intermediates delivers difluorobenzylic radicals that can be intercepted by abundant alkene feedstocks or a hydrogen atom to provide a diverse array of difluoalkylaromatics.
gem-Difluorination of 1,3-dithiolanes with the hexafluoropropene-diethylamine reagent and N-iodosuccinimide or 1,3-dibromo-5,5-dimethylhydantoin
Shimizu, Makoto,Maeda, Takashi,Fujisawa, Tamotsu
, p. 9 - 12 (2007/10/02)
gem-Difluoro compounds are readily prepared from 1,3-dithiolanes in good yield on treatment with hexafluoropropene-diethylamine/1,3-dibromo-5,5-dimethylhydantoin or /N-iodosuccinimide/water. - Keywords: gem-Difluorination; 1,3-Dithiolanes; NMR spectroscop
Conversion of the Carbonyl Group to CF2 Using IF
Rozen, Shlomo,Zamir, Dov
, p. 4695 - 4700 (2007/10/02)
A novel method for the transformation of CO -> CF2 is described.The easily made hydrazone derivatives of the carbonyl moiety are reacted under mild conditions with IF prepared directly from the corresponding elements.Various hydrazones have been examined and compared with each other.Unsubstituted ones are usually the most suitable although they are not always easy to purify and store.N-Methyl- and N,N-dimethylhydrazones also give quite satisfactory results.The more easily made dinitrophenyl hydrazones (DNPs), semicarbazones, and tosylhydrazones also react, but the yields of the desired CF2 compounds are usually lower.Oximes could also be successfully reacted.The two main byproducts of the reaction are the parent carbonyl compounds, which can be recycled, and the α-iododifluoro derivatives.The latter upon treatment with LiAlH4 or Bu3SnH were reduced to the desired product, thus increasing the overall yields.
