120120-26-5Relevant articles and documents
Preparation of tri- and difluoromethylsilanes via an unusual magnesium metal-mediated reductive tri- and difluoromethylation of chlorosilanes using tri- and difluoromethyl sulfides, sulfoxides, and sulfones
Prakash, G.K. Surya,Hu, Jinbo,Olah, George A.
, p. 4457 - 4463 (2003)
A new and efficient method for the preparation of tri- and difluoromethylsilanes using magnesium metal-mediated reductive tri- and difluoromethylation of chlorosilanes is reported using tri- and difluoromethyl sulfides, sulfoxides, and sulfones. The byproduct of the process is diphenyl disulfide. Since phenyl trifluoromethyl sulfone, sulfoxide, and sulfide are readily prepared from trifluoromethane (CF3H) and diphenyl disulfide, the method can be considered to be catalytic in diphenyl disulfide for the preparation of (trifluoromethyl)trimethylsilane (TMS-CF3) from non-ozone-depleting trifluoromethane.
DIRECT TRIFLUOROMETHYLATIONS USING TRIFLUOROMETHANE
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Paragraph 0058, (2014/03/25)
A direct trifluoromethylation method preferably using a trifluoromethane as a fluoro-methylating species. In particular, the present method is used for preparing a trifluoromethylated substrate by reacting a fluoromethylatable substrate with a trifiuoromethylating agent in the presence of an alkoxide or metal salt of silazane under conditions sufficient to trifluoromethylate the substrate; wherein the fluoromethylatable substrate includes chlorosilanes, carbonyl compounds such as esters, aryl halides, aldehydes, ketones, chalcones, alkyl formates, alkyl halides, aryl halides, alkyl borates, carbon dioxide or sulfur.
Taming of fluoroform: Direct nucleophilic trifluoromethylation of Si, B, S, and C centers
Surya Prakash,Jog, Parag V.,Batamack, Patrice T. D.,Olah, George A.
, p. 1324 - 1327 (2013/02/22)
Fluoroform (CF3H), a large-volume by-product of the manufacture of Teflon, refrigerants, polyvinylidene fluoride (PVDF), fire-extinguishing agents, and foams, is a potent and stable greenhouse gas that has found little practical use despite the growing importance of trifluoromethyl (CF3) functionality in more structurally elaborate pharmaceuticals, agrochemicals, and materials. Direct nucleophilic trifluoromethylation using CF3H has been a challenge. Here, we report on a direct trifluoromethylation protocol using close to stoichiometric amounts of CF3H in common organic solvents such as tetrahydrofuran (THF), diethyl ether, and toluene. The methodology is widely applicable to a variety of silicon, boron, and sulfur-based electrophiles, as well as carbon-based electrophiles.
Magnesium mediated preparation of fluorinated alkyl silanes
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, (2008/06/13)
An efficient method is disclosed for the preparation of trifluoromethyl- and difluoromethylsilanes using magnesium metal mediated reductive tri- and difluoromethylation of chlorosilanes with tri- and difluoromethyl sulfides, sulfoxides, and sulfones. One
Acetic acid derivatives and their production
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, (2008/06/13)
Compounds of formula STR1 where n is an integer from 1 to 12, R and R1 are the same or different and are hydrogen or C1 to C6 linear or branched alkyl as well as their physiologically active salts and amides thereof and the enantiomers, mixtures and racemates are disclosed. Intermediates useful in preparing the above compounds are also disclosed as are processes for preparing these compounds.
Trifluoromethylation of carbonyl compounds
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, (2008/06/13)
A process which comprises reacting under substantially anhydrous conditions a perfluoroalkyltrihydrocarbylsilane and a carbonyl compound in the presence of a catalyst such that the carbonyl compound is perfluoroalkylated.
Gem-disubstituted cyclohexadienones and their production
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, (2008/06/13)
Quinones may be perfluoroalkylated by means of perfluoroalkyltrihydrocarbyl silane using certain active alkali metal salt catalysts devoid of fluorine (e.g., LiN3, NaN3, KN3, NaCN KCN, CsCN, NaOH, KOH, K2 CO3, and Cs2 CO3). The reaction--which is conducted under essentially anhydrous conditions, preferably in a suitable liquid phase reaction medium, most preferably a dipolar aprotic solvent--results in the formation of gem-disubstituted cyclohexadienones in which the gem substituents are a perfluoroalkyl group and a trihydrocarbylsiloxy group. These gem-disubstituted compounds in turn can be readily converted to perfluoroalkyl substituted aromatics, thus circumventing the traditional need for photochlorination followed by halogen exchange using hydrogen fluoride as a means of preparing perfluoroalkyl aromatic compounds.
A New Method for Synthesis of Trifluoromethyl-Substituted Phenols and Anilines
Stahly, G. Patrick,Bell, Donald R.
, p. 2873 - 2877 (2007/10/02)
Triethyl(trifluoromethyl)silane and tri-n-butyl(trifluoromethyl)silane were found to react with quinones by addition to one of the carbonyl carbon atoms, giving dienones containing geminal trifluoromethyl and trialkylsiloxy substituents.These reactions were catalyzed by a variety of basic compounds.Quinones found to undergo this process include 1,2- and 1,4-benzoquinones (some bearing alkyl substituents), naphthoquinone, anthraquinone, and phenanthrenequinone.Most of the resulting dienones gave (trifluoromethyl)phenols on dissolving matal reduction, and one was subjected to reductive amination to give (trifluoromethyl)aniline.
