- Metal-Free Construction of the C(sp3)-CF3 Bond: Trifluoromethylation of Hydrazones with Togni's Reagent under Mild Conditions
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A metal-free trifluoromethylation of hydrazones with Togni's reagent under mild conditions was developed. Various functional groups including ester, methoxy, dimethoxy, nitro, halogen, and heterocyclic compounds were tolerated. This simple and green strategy provides a practical tool to construct C(sp3)-CF3 bonds.
- Zeng, Huiying,Luo, Zhen,Han, Xinlong,Li, Chao-Jun
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supporting information
p. 5948 - 5951
(2019/08/29)
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- Denitrogenative Hydrotrifluoromethylation of Benzaldehyde Hydrazones: Synthesis of (2,2,2-Trifluoroethyl)arenes
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Reacting hydrazones of arylaldehydes with Togni's CF3-benziodoxolone reagent, in the presence of potassium hydroxide and cesium fluoride, induces a denitrogenative hydrotrifluoromethylation event to produce (2,2,2-trifluoroethyl)arenes. This novel reaction was tolerant to many electronically-diverse functional groups and substitution patterns, as well as naphthyl- and heteroaryl-derived substrates. Advantages of this process include the easy access to hydrazone precursors on a large scale, speed and operational simplicity, and being transition metal-free.
- Zhao, Zhensheng,Ma, Kevin C. Y.,Legault, Claude Y.,Murphy, Graham K.
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p. 11240 - 11245
(2019/08/20)
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- A facile synthesis of isomeric C -(2,2,2-trifluoroethyl)anilines
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Three isomers of C-(2,2,2-trifluoroethyl)aniline were prepared on a multigram scale from readily available nitrophenylacetic acids in two steps. First, the carboxy groups of the latter were converted into the trifluoromethyl moieties by treatment with sul
- Trofymchuk, Sergii,Bezdudny, Andrii V.,Pustovit, Yurii M.,Lukin, Oleg,Boyko, Alexander N.,Chekotylo, Alexey,Tolmachev, Andrei A.,Mykhailiuk, Pavel K.
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experimental part
p. 1974 - 1976
(2012/08/27)
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- Cu-mediated chemoselective trifluoromethylation of benzyl bromides using shelf-stable electrophilic trifluoromethylating reagents
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Copper-mediated chemoselective trifluoromethylation at the benzylic position by the use of shelf-stable electrophilic trifluoromethylating reagents 3 in good to high yields under mild conditions is described for the first time. The generality of this trifluoromethylation for a wide variety of benzyl bromides facilitates the rapid creation of structural diversity of medicinal candidates in drug discovery.
- Kawai, Hiroyuki,Furukawa, Tatsuya,Nomura, Yoshinori,Tokunaga, Etsuko,Shibata, Norio
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supporting information; experimental part
p. 3596 - 3599
(2011/09/16)
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- The reactions of copper-dibromodifluoromethane-amide systems with alcohols
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1,1,1-Trifluoro-2-arylethanes can be prepared by the trifluoromethyldehydroxylation of benzyl alcohols using the copper-dibromodifluoromethane-amide reaction system, although the yields are low.The mechanism of the reaction may involve chelation of the substrate to copper so that α-substituted benzyl alcohols and other alcohols are unreactive.
- Clark, James H.,McClinton, Martin A.,Blade, Robert J.
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p. 257 - 267
(2007/10/02)
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