743437-79-8Relevant academic research and scientific papers
Rapid and efficient trifluoromethylation of aromatic and heteroaromatic compounds using potassium trifluoroacetate enabled by a flow system
Chen, Mao,Buchwald, Stephen L.
supporting information, p. 11628 - 11631 (2013/11/06)
Going to the source: The trifluoromethylation of aryl/heteroaryl iodides has been demonstrated using a flow system, thus enabling a rapid rate of reaction. A broad spectrum of trifluoromethylated compounds was prepared in good to excellent yields using CF3CO2K as the trifluoromethyl source. The process has the advantage of short reaction times and uses convenient [CF3] sources. Copyright
Discovery of 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride as a deoxofluorinating agent with high thermal stability as well as unusual resistance to aqueous hydrolysis, and its diverse fluorination capabilities including deoxofluoro-arylsulfinylation with high stereoselectivity
Umemoto, Teruo,Singh, Rajendra P.,Xu, Yong,Saito, Norimichi
supporting information; scheme or table, p. 18199 - 18205 (2011/03/18)
Versatile, safe, shelf-stable, and easy-to-handle fluorinating agents are strongly desired in both academic and industrial arenas, since fluorinated compounds have attracted considerable interest in many areas, such as drug discovery, due to the unique effects of fluorine atoms when incorporated into molecules. This article describes the synthesis, properties, and reactivity of many substituted and thermally stable phenylsulfur trifluorides, in particular, 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride (Fluolead, 1k), as a crystalline solid having surprisingly high stability on contact with water and superior utility as a deoxofluorinating agent compared to current reagents, such as DAST and its analogues. The roles of substiuents on 1k in thermal and hydrolytic stability, fluorination reactivity, and the high-yield fluorination mechanism it undergoes have been clarified. In addition to fluorinations of alcohols, aldehydes, and enolizable ketones, 1k smoothly converts non-enolizable carbonyls to CF2 groups, and carboxylic groups to CF3 groups, in high yields. 1k also converts C(=S) and CH3SC(=S)O groups to CF2 and CF3O groups, respectively, in high yields. In addition, 1k effects highly stereoselective deoxofluoro-arylsulfinylation of diols and amino alcohols to give fluoroalkyl arylsulfinates and arylsulfinamides, with complete inversion of configuration at fluorine and the simultaneous, selective formation of one conformational isomer at the sulfoxide sulfur atom. Considering the unique and diverse properties, relative safety, and ease of handling of 1k in addition to its convenient synthesis, it is expected to find considerable use as a novel fluorinating agent in both academic and industrial arenas.
METHODS AND COMPOSITIONS FOR PRODUCING DIFLUOROMETHYLENE-AND TRIFLUOROMETHYL-CONTAINING COMPOUNDS
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Page/Page column 31, (2009/07/17)
New methods for producing difluoromethylene-containing compounds with phenylsulfur trifluoride or a primary alkyl-substituted phenylsulfur trifluoride are disclosed. Also, new methods for producing trifluoromethyl-containing compounds with phenylsulfur trifluoride or primary alkyl-substituted phenylsulfur trifluoride are also disclosed.
FLUORINATION PROCESSES WITH ARYLSULFUR HALOTETRAFLUORIDES
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Page/Page column 49, (2009/10/22)
New fluorination processes for introducing one or more fluorine atoms into target substrate compounds with arylsulfur halotetrafluorides are disclosed. Also disclosed are methods for preparation of arylsulfur trifluorides.
SUBSTITUTED PHENYLSULFUR TRIFLUORIDE AND OTHER LIKE FLUORINATING AGENTS
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Page/Page column 21-23, (2008/06/13)
Novel substituted phenylsulfur trifluorides that act as fluorinating agents are disclosed. Also disclosed are methods for their preparation and methods for their use in introducing one or more fluorine atoms into target substrate compounds.
Substituted phenylsulfur trifluoride and other like fluorinating agents
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Page/Page column 21 - 22, (2008/06/13)
Novel substituted phenylsulfur trifluorides that act as fluorinating agents are disclosed. Also disclosed are methods for their preparation and methods for their use in introducing one or more fluorine atoms into target substrate compounds.
