26946-13-4Relevant academic research and scientific papers
Stereodivergent hydrodefluorination of: Gem -difluoroalkenes: Selective synthesis of (Z)- and (E)-monofluoroalkenes
Kojima, Ryoto,Kubota, Koji,Ito, Hajime
supporting information, p. 10688 - 10691 (2017/10/06)
We have developed a novel approach for the stereodivergent hydrodefluorination of gem-difluoroalkenes using copper(i) catalysts to obtain stereodefined monofluoroalkenes. Both (Z)- and (E)-terminal monofluoroalkenes were obtained by the hydrodefluorination of gem-difluoroalkenes in the presence of copper(i) catalysts and diboron or hydrosilane, respectively, with high stereoselectivity. DFT calculations were conducted to elucidate the stereoselectivity.
Decarboxylation and fluorination method for cinnamic acid and derivative thereof
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Paragraph 0045; 0046, (2017/02/24)
The invention discloses a decarboxylation and fluorination method for cinnamic acid and a derivative thereof. The method comprises the steps that the cinnamic acid or the derivative thereof reacts with 1-chloromethyl-4-fluorophenyl-1,4-diazabicyclo[2.2.2]octane bis(tetrafluoroboric acid) salt and an alkali compound in one pot, and the fluorination product (mainly a cis-form structure product) of the cinnamic acid or the derivative thereof is obtained. The method fills in the technical blank on the decarboxylation and fluorination method for carboxylic acid connected with SP2 hybridization carbon atoms in the prior art, and is easy to operate, short in process and high in product yield, and the industrial production requirement is met.
Transition metal free decarboxylative fluorination of cinnamic acids with selectfluor
Li, Cheng-Tan,Yuan, Xi,Tang, Zhen-Yu
supporting information, p. 5624 - 5627 (2016/11/28)
Herein we report a transition metal free decarboxylative fluorination of cinnamic acids with selectfluor. A range of functionalized cinnamic acid derivatives reacted with 2 equiv. of selectfluor and 4 equiv. of base in hydrophobic solvent and water to afford β-fluorostyrene with good yield and Z-stereoselectivity. Kinetic study was conducted.
Stereoselective synthesis of both stereoisomers of β-fluorostyrene derivatives from a common intermediate
Landelle, Gregory,Turcotte-Savard, Marc-Olivier,Angers, Laetitia,Paquin, Jean-Francois
, p. 1568 - 1571 (2011/04/26)
The stereoselective synthesis of both cis- and trans-β-fluorostyrene derivatives from a common intermediate, (Z)-1-aryl-2-fluoro-1-(trimethylsilyl) ethenes, is described. The trans isomers are obtained by a stereospecific replacement of the silyl group in
Monofluorovinyl tosylate: A useful building block for the synthesis of terminal vinyl monofluorides via suzuki-Miyaura coupling
Zhang, He,Zhou, Chang-Bing,Chen, Qing-Yun,Xiao, Ji-Chang,Hong, Ran
supporting information; experimental part, p. 560 - 563 (2011/04/23)
Monofluorovinyl tosylate was developed as a practical vinyl fluoride building block to couple with a variety of arylboronic acids in the presence of a palladium catalyst. The high stereoselectivity of 2-aryl-1-fluoroethene derivatives was achieved. This a
Synthesis of monofluoroalkenes via Julia-Kocienski reaction
Prakash, G.K. Surya,Shakhmin, Anton,Zibinsky, Mikhail,Ledneczki, Istvan,Chacko, Sujith,Olah, George A.
experimental part, p. 1192 - 1197 (2011/02/22)
Monofluoromethyl 3,5-bis(trifluoromethyl)phenyl sulfone 1 was synthesized and employed in Julia-Kocienski fluoroolefination reaction with various ketones and aldehydes. Optimal reaction conditions were found to be the treatment of substrates with KOH or C
A simple, two-step, site-specific preparation of fluorinated naphthalene and phenanthrene derivatives from fluorobromo-substituted alkenes
Wang, Yi,Xu, Jianjun,Burton, Donald J.
, p. 7780 - 7784 (2007/10/03)
(Chemical Equation Presented) A facile two-step procedure for the site-specific preparation of fluorinated naphthalene and phenanthrene derivatives is described. The Sonogashira reaction of bromofluoro-substituted alkenes with terminal alkynes, followed b
Site-specific preparation of 3-fluoro-1-substituted-naphthalenes via a novel base-catalyzed cyclization reaction from (E)-monofluoroenynes
Xu, Jianjun,Wang, Yi,Burton, Donald J.
, p. 2555 - 2558 (2007/10/03)
A novel cyclization reaction for the preparation of 3-fluoro-1-substituted- naphthalenes is reported. (E)-Monofluoroenynes, which are prepared by Sonogashira coupling reaction from (Z)-1-bromo-1-fluoroalkenes, undergo cyclization to afford 3-fluoro-1-subs
Synthesis and Horner-Wittig Chemistry of (Fluoromethyl)diphenylphosphane Oxide
Steenis, Jan Hein van,Gen, Arne van der
, p. 897 - 910 (2007/10/03)
(Fluoromethyl)diphenylphosphane oxide (1) was obtained by heating (diphenylphosphinoyl)methyl p-toluenesulfinate (2) with potassium fluoride. Compound 1 is a stable, crystalline solid, suitable for application in the Horner-Wittig reaction. The compound described in the literature under this name was found to be benzylphenylphosphinic fluoride (5). The anion of phosphane oxide 1 readily reacted with a wide range of carbonyl to yield diastereomeric mixtures of α-fluoro-β-(hydroxyalkyl)phosphane oxides (7), which in most cases could be separated. The ease of phosphinate elimination to yield (E)- and (Z)-1-fluoroalkenes 8 stereoselectively was found to be strongly dependent upon conformation and substituent patern. The route presented here avoids the use of hazardous fluorohalomethanes, which were employed in several earlier Wittig-related approaches to vinyl fluorides.
Generation of acetylides by treatment of fluoroethylenes with LDA: Preparation of propargyl alcohols
Kataoka, Kentaro,Tsuboi, Sadao
, p. 452 - 456 (2007/10/03)
The fluoroethylenes 3 produced the corresponding acetylides via dehydrofluorination and deprotonation by treatment with 2 equivalents of LDA in THF at 0 °C. These acetylides reacted with aldehydes and ketones to afford propargyl alcohols in good yields.
