- Synthesis and Reactivity of α-Cumyl Bromodifluoromethanesulfenate: Application to the Radiosynthesis of [18F]ArylSCF3
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A highly reactive electrophilic bromodifluoromethylthiolating reagent, α-cumyl bromodifluoro-methanesulfenate 1, was prepared to allow for direct bromodifluoromethylthiolation of aryl boron reagents. This coupling reaction takes place under copper catalysis, and affords a large range of bromodifluoromethylthiolated arenes. These compounds are amenable to various transformations including halogen exchange with [18F]KF/K222, a process giving access to [18F]arylSCF3 in two steps from the corresponding aryl boronic pinacol esters.
- Wu, Jiang,Zhao, Qunchao,Wilson, Thomas C.,Verhoog, Stefan,Lu, Long,Gouverneur, Véronique,Shen, Qilong
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supporting information
p. 2413 - 2417
(2019/02/01)
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- (Bromodifluoromethyl)thioxo compound, intermediate as well as preparation method and application of compound
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The invention discloses a (bromodifluoromethyl)thioxo compound, an intermediate as well as a preparation method and application of the compound. The invention provides a compound I, wherein R1, R2 and R3 are respectively independently H, C1-C10 alkyl and C6-C10 aryl, and at least two of R1, R2 and R3 are not H at the same time; any two of R1, R2 and R3 are connected to form a C3-C6 cycloalkane; or any two of R1, R2 and R3 are connected to from a C3-C6 cycloalkane, and then the C3-C6 cycloalkane and a benzene ring form a parallel loop. The preparation method of the compound I provided by the invention comprises the following step: in an organic solvent, carrying out reaction on a compound II, Cl2 and a compound III, so that the compound I is obtained. By adopting the (bromodifluoromethyl)thioxo compound I, direct introduction of (bromodifluoromethyl)thio on an aromatic hydrocarbon or hetero-aromatic hydrocarbon compound can be realized. (The structure of the compound I is described in the specification.).
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Paragraph 0116-0118
(2017/09/01)
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- Electrophilic difluoro(phenylthio)methylation: Generation, stability, and reactivity of α-fluorocarbocations
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Electrophilic difluoro(phenylthio)methylation of allylsilanes has been achieved using bromodifluoro(phenylthio)methane (PhSCF2Br) and silver hexafluoroantimonate (AgSbF6). The structural assignment and observation of α-fluorocarbocation were substantiated by NMR and theoretical calculations. Detailed mechanistic and electronic studies have provided a fundamental understanding of the reactivity and stability of the difluoro(phenylthio)methylium cation (PhSCF2+).
- Betterley, Nolan M.,Surawatanawong, Panida,Prabpai, Samran,Kongsaeree, Palangpon,Kuhakarn, Chutima,Pohmakotr, Manat,Reutrakul, Vichai
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supporting information
p. 5666 - 5669
(2013/12/04)
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- Efficient synthesis of unsymmetrical S-(bromodifluoromethyl)diarylsulfonium salts for electrophilic bromodifluoromethylating reagents
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A series of unsymmetrical S-(bromodifluoromethyl)diarylsulfonium salts 1 were readily synthesized by treatment of corresponding (bromodifluoromethyl) arylsulfoxides 2 and substituted benzenes 3 with triflic anhydride in moderate to good yields. The unsymmetrical sulfonium salts 1 with different aryl groups having electron-donating or electron-withdrawing substituents can be nicely constructed depending on the choice of 2 and 3. Bromodifluoromethylation of alkynes was evaluated by using the selected diarylsulfonium salts 1 to provide the desired bromodifluoromethylated alkynes in moderate to good yields.
- Liu, Guokai,Mori, Satoru,Wang, Xin,Noritake, Shun,Tokunaga, Etsuko,Shibata, Norio
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supporting information; experimental part
p. 1769 - 1773
(2012/10/08)
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- Insecticidal 3-difluoromethoxyphenyl-1-phenylcarbamoyl-2-pyrazolines
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Pyrazoline derivatives useful as insecticides having the formula STR1 wherein R1 represents hydrogen atom, a lower alkyl group, (CH2)n CN group, (CH2)n OR group, phenyl group or a halogen-substituted phenyl group; R2 represents hydrogen atom or methyl group; Y represents hydrogen atom or chlorine atom; X represents oxygen atom, sulfur atom, sulfinyl or sulfonyl group; R3 represents a halogen-substituted lower alkyl group; and n is integer 1 to 3 and R represents a lower alkyl group.
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- PREPARATION OF BROMODIFLUOROMETHYL SULFIDE AND ITS CONVERSION TO TRIFLUOROMETHYL SULFIDE
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Bromodifluoromethyl sulfides are prepared by the reaction of mercaptides with CF2BrX (x=Br,Cl).And treatment of bromodifluoromethyl sulfides with various inorganic fluorides produced trifluoromethyl sulfides.
- Suda, Minoru,Hino, Chiaki
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p. 1997 - 2000
(2007/10/02)
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- SYNTHESE DE COMPOSES AROMATIQUES COMPORTANT LES GROUPEMENTS OCF2Br ET SCF2Br-II; ACTION DE CF2Br2 ET DE CF2BrCl SUR DES THIOPHENATES ET PHENATES DE POTASSIUM DIVERSEMENT SUBSTITUES
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The reaction of dibromodifluoromethane and bromochlorodifluoromethane with substituted potassium thiophenoxides and phenoxides leads to the formation of new aromatic compounds bearing OCF2Br and SCF2Br groups.
- Rico, I,Wakselman, C.
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p. 4209 - 4214
(2007/10/02)
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