- Corey-Chaykovsky Reactions of Nitro Styrenes Enable cis-Configured Trifluoromethyl Cyclopropanes
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Trifluoromethyl-substituted cyclopropanes are an attractive family of building blocks for the construction of pharmaceutical and agrochemical agents. This work demonstrated the utilization of fluorinated sulfur ylides as versatile reagents for Corey-Chaykovsky cyclopropanation reactions of nitro styrenes. This protocol favored the synthesis of cis-configured trifluoromethyl cyclopropanes for a broad range of substrates with excellent yields and good diastereoselectivities.
- Hock, Katharina J.,Hommelsheim, Renè,Mertens, Lucas,Ho, Junming,Nguyen, Thanh V.,Koenigs, Rene M.
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- Solvent-free synthesis of alkyl and fluoroalkyl sulfonium salts from sulfides and fluoroalkyl trifluoromethanesulfonates
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A series of diaryl(fluoroalkyl)sulfonium salts were synthesized from electron-rich diaryl sulfides and fluoroalkyl trifluoromethanesulfonates under solvent-free conditions. Unlike diaryl sulfides, dialkyl and alkyl(aryl) sulfides reacted with fluoroalkyl
- Song, Hai-Xia,Wang, Shi-Meng,Wang, Xiao-Yan,Han, Jia-Bin,Gao, Ying,Jia, Su-Jiao,Zhang, Cheng-Pan
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- Diastereoselective Synthesis of CF3-Containing Vicinal Diamines
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The highly diastereoselective synthesis of CF3-containing vicinal diamines by a convenient two-step procedure without the need to isolate the intermediate products is described.
- Huang, Qiu-Xia,Zheng, Qu-Tong,Duan, Yaya,Lin, Jin-Hong,Xiao, Ji-Chang,Zheng, Xing
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- PESTICIDALLY ACTIVE AZOLE-AMIDE COMPOUNDS
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Compounds of formula (I) wherein the substituents are as defined in claim 1, and the agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds, can be used as insecticides.
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Page/Page column 93; 94
(2020/09/30)
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- PESTICIDALLY ACTIVE DIAZINE-AMIDE COMPOUNDS
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Compounds of formula I (Formula I) wherein the substituents are as defined in claim 1, and the agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds, can be used as insecticides.
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Page/Page column 79; 80
(2020/10/20)
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- N-[1-(5-BROMO-2-PYRIMIDIN-2-YL-1,2,4-TRIAZOL-3-YL)ETHYL]-2-CYCLOPROPYL-6-(TRIFLUOROMETHYL)PYRIDINE-4-CARBOXAMIDE DERIVATIVES AND RELATED COMPOUNDS AS INSECTICIDES
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Compounds of formula (I) wherein the substituents are as defined in claim 1, and the agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds, can be used as insecticides.
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Page/Page column 79; 80; 81
(2020/10/17)
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- PESTICIDALLY ACTIVE DIAZINE-AMIDE COMPOUNDS
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Compounds of formula I (l) wherein the substituents are as defined in claim 1, and the agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds, can be used as insecticides.
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Page/Page column 81
(2020/10/20)
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- PESTICIDALLY ACTIVE AZOLE AMIDE COMPOUNDS
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Compounds of formula (I) wherein the substituents are as defined in claim 1, and the agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds, can be used as insecticides.
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Page/Page column 77
(2020/10/09)
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- Fluorine-containing three-membered ring compound, preparation method of fluorine-containing three-membered ring compound and preparation method of fluoroalkyl sulfonium salt
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The invention discloses a fluorine-containing three-membered ring compound shown in the formula V-a, V-b or V-c and a preparation method thereof. The preparation method comprises that in an organic solvent, fluoroalkyl sulfur ylide shown in the formula II
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Paragraph 0238; 0239; 0240; 0241; 0242
(2016/10/08)
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- Pd-catalyzed Suzuki–Miyaura cross-coupling of [Ph2SR][OTf] with arylboronic acids
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The Pd-catalyzed Suzuki–Miyaura cross-coupling of alkyl- and fluoroalkyl(diphenyl)sulfonium triflates with arylboronic acids was compared. The fluorine substitution on the alkyl groups of [Ph2SR][OTf] had a big influence on the reaction. Perfluoroalkyl(diphenyl)sulfonium triflates (2b–d) were unsuccessful participants in the Pd-catalyzed phenylation of arylboronic acid under the standard conditions because of the strong electronegativity of the long-chain perfluoroalkyl groups, which underwent S[sbnd]Rfnbond cleavage instead. Polyfluoroalkyl(diphenyl)sulfonium triflates (2f–h) reacted with arylboronic acid to afford the phenylation product in very low yields due to the tendency of deprotonation and β-F elimination of the sulfonium salts. Eventually, (2,2,2-trifluoroethyl)diphenylsulfonium triflate (2e), methyl- or ethyl(diphenyl)sulfonium triflate (2i or 2j), and triphenylsulfonium triflate (2m) were found to be more effective reagents than other tested phenylsulfounium salts for Pd-catalyzed phenylation, which provided much higher yields of the desired products under mild conditions.
- Wang, Xiao-Yan,Song, Hai-Xia,Wang, Shi-Meng,Yang, Jing,Qin, Hua-Li,Jiang, Xin,Zhang, Cheng-Pan
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p. 7606 - 7612
(2016/11/11)
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- Diastereoselective Johnson-Corey-Chaykovsky trifluoroethylidenation
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(2,2,2-Trifluoroethyl)diphenylsulfonium triflate was found to be an efficient ylide reagent for the Johnson-Corey-Chaykovsky reaction to afford trifluoromethyl epoxides, cyclopropanes and aziridines. Interestingly, excellent but different diastereoselectivity was observed for these transformations. Both trifluoromethyl epoxides and cyclopropanes were obtained with trans-selectivity, whereas aziridines were obtained with cis-selectivity.
- Duan, Yaya,Zhou, Bin,Lin, Jin-Hong,Xiao, Ji-Chang
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supporting information
p. 13127 - 13130
(2015/08/18)
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- Synthesis of 2,2,2-Trifluoroethylated Onium Salts of Nitrogen, Sulfur, and Phosphorus with (2,2,2-Trifluoroethyl)phenyliodonium Triflate
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Various 2,2,2-trifluoroethyl onium triflates were synthesized by treating tertiary amines, pyridines, quinoline, a triazole, sulfides, and a phosphine with (2,2,2-trifluoroethyl)phenyliodonium triflate.Sulfoxides and N-oxide were converted to the correspo
- Umemoto, Teruo,Gotoh, Yoshihiko
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p. 2008 - 2010
(2007/10/02)
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