78960-83-5Relevant academic research and scientific papers
Electroreductive coupling of halofluoro compounds with aldehydes
Shono,Kise,Oka
, p. 6567 - 6570 (1991)
Electroreductive intermolecular coupling of halofluoro compounds such as 1,1,1-trichloro-2,2,2-trifluoroethane, methyl chlorodifluoroacetate, and perfluoroalkyl halides with aldehydes took place effectively in the presence of chlorotrimethylsilane and one of the coupling products, 2,2-dichloro-3,3,3-trifluoro-1-phenyl-1-propranol, was selectively convertible to a variety of compounds with using the electroreduction as a key reaction.
Barbier-type reaction of fluoroalkyl iodides with aldehydes without activation
Shen, Yanchang,Qi, Ming
, p. 175 - 178 (1994)
Fluoroalkyl iodides react with aldehydes in the presence of zinc in N,N-dimethylacetamide without activation, giving a variety of fluoroalkylated carbinols in 72percent-90percent yield.The reaction provides a convenient method for the synthesis of these c
Perfluoroalkyl and -aryl Zinc Ate Complexes: Generation, Reactivity, and Synthetic Application
Wang, Xuan,Hirano, Keiichi,Kurauchi, Daisuke,Kato, Hisano,Toriumi, Naoyuki,Takita, Ryo,Uchiyama, Masanobu
supporting information, p. 10993 - 10996 (2015/11/10)
A combination of dimethylzinc, perfluoroalkyl iodide, and LiCl afforded a new type of perfluoroalkyl (RF) zinc ate complex. These complexes show much greater thermal stability than conventional perfluorinated metal species, such as RF-lithium species and Grignard reagents, and they can be used at room temperature or higher. The results of DFT calculations on the origin of the enhanced stability are reported and the synthetic utility of RF-zincate complexes is demonstrated. The magnificent ate: A combination of dimethylzinc, perfluoroalkyl iodide, and LiCl afforded a new type of perfluoroalkyl (RF) zinc ate complex. These complexes show greater thermal stability than conventional perfluorinated metal species and they can be used at room temperature or higher. The results of DFT calculations on the origin of the enhanced stability are reported and the synthetic utility of RF-zincate complexes is demonstrated.
Method for Producing Fluorine-Containing Substituted Compound and Fluorine-Containing Substituted Compound
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Paragraph 0240-0254, (2014/02/15)
A method for producing a fluorine-containing substituted compound, the method including: introducing an organofluorine compound and an organolithium compound into a microreactor provided with a flow path capable of mixing a plurality of liquids, to thereby obtain a reaction product; and introducing, into the microreactor, the reaction product and an electrophile exhibiting electrophilic effect on the reaction product, to thereby obtain a fluorine-containing substituted compound.
Perfluoroalkylation in flow microreactors: Generation of perfluoroalkyllithiums in the presence and absence of electrophiles
Nagaki, Aiichiro,Tokuoka, Shinya,Yamada, Shigeyuki,Tomida, Yutaka,Oshiro, Kojun,Amii, Hideki,Yoshida, Jun-Ichi
supporting information; experimental part, p. 7559 - 7563 (2011/12/03)
Perfluoroalkyllithiums were effectively generated from perfluoroalkyl halides in the presence and absence of electrophiles using flow microreactor systems. The in situ trapping with electrophile is conducted at much higher temperatures than those required for batch macro reactors. The subsequent trapping method is quite effective for highly reactive electrophiles that are not compatible with the lithiation process.
Tandem reductive perfluoroalkylation of esters with perfluoroalkyl titanate-type reagents
Mikami, Koichi,Murase, Tatsushi,Itoh, Yoshimitsu
, p. 11686 - 11687 (2008/03/13)
The generation of stable perfluoroalkyl titanate-type reagents and their new type of reaction, tandem reductive perfluoroalkylation of esters, are shown to give perfluoroalkylated sec-alcohols in up to quantitative yield. Copyright
Nucleophilic perfluoroalkylation of aldehydes, ketones, imines, disulfides, and diselenides
Pooput, Chaya,Dolbier Jr., William R.,Medebielle, Maurice
, p. 3564 - 3568 (2007/10/03)
Using a procedure analogous to that developed for nucleophilic trifluoromethylation, the perfluoroalkyl anion reagents created by mixing C 2F5I and n-C4F9I with tetrakis(dimethylamino)ethylene (TDAE) were effective in their nucleophilic reactions with aldehydes, ketones, imines, disulfides, and diselenides. Irradiation proved beneficial in the aldehyde and ketone reactions.
Barbier-type addition of alkyl halides to aldehydes promoted by pentacarbonyliron
Vasil'Eva,Mysova,Chakhovskaya,Terent'Ev
, p. 1014 - 1017 (2007/10/03)
The yield and structure of products of the Barbier-type addition of alkyl halides (perfluorobutyl iodide, allyl bromide, allyl iodide, and hexyl iodide) to para-substituted benzaldehydes in the presence of pentacarbonyliron are essentially determined, on the one hand, by the ability of alkyl halide to be reduced to carbanion and, on the other, by the electrophilicity of the aldehyde reaction center which in turn depends on the nature of para-substituent in the aromatic ring.
Ultrasound-Promoted Selective Perfluoroalkylation on the Desired Position of Organic Molecules
Kitazume, Tomoya,Ishikawa, Nobuo
, p. 5186 - 5191 (2007/10/02)
Perfluoroalkylzinc iodides or bromides wich were prepared from perfluoroalkyl iodides or bromides and zinc powder in N,N-dimethylformamide or tetrahydrofuran with ultrasonic irradiation were found to behave as potential perfluoroalkylating reagents for the preparation of a wide variety of perfluoroalkylated compounds.Especially, the ultrasound-promoted asymmetric induction with perfluoroalkyl group on the asymmetrical carbon was achieved by the reaction of perfluoroalkyl halides with optically active enamines in the presence of zinc powder and a catalytic amount of dichlorobis(?-cyclopentadienyl)titanium.
