390-75-0Relevant academic research and scientific papers
Synthesis of α-fluoro-β-lactones and their thermal conversion to 1-fluoroalkenes
Ocampo, Rogelio,Dolbier Jr., William R.,Zuluaga, Fabio
, p. 1325 - 1334 (2002)
α-Fluoro-β-lactones have been synthesized and isolated for the first time from α-fluoro-β-hydroxy acids by using the couple TsCl/DMAP as lactonization agent. A detailed description of the synthesis and spectroscopic properties of α-fluoro-β-lactones is pr
Iodine-catalyzed transformation of aryl-substituted alcohols under solvent-free and highly concentrated reaction conditions
Jereb, Marjan,Vra?i?, Dejan
, p. 747 - 762 (2018/01/17)
Iodine-catalyzed transformations of alcohols under solvent-free reaction conditions (SFRC) and under highly concentrated reaction conditions (HCRC) in the presence of various solvents were studied in order to gain insight into the behavior of the reaction intermediates under these conditions. Dimerization, dehydration and substitution were the three types of transformations observed with benzylic alcohols. Dimerization and substitution reactions were predominant in the case of primary- and secondary alcohols, whereas dehydration prevailed in the case of tertiary alcohols. The relative reactivity of substituted 1-phenylethanols in I2-catalyzed dimerization under SFRC provided a good Hammett plot ρ+ = -2.8 (r2 = 0.98), suggesting the presence of electron-deficient intermediates with a certain degree of developed charge in the rate-determining step.
Palladium-Catalyzed Fluorination of Cyclic Vinyl Triflates: Effect of TESCF3as an Additive
Ye, Yuxuan,Takada, Takashi,Buchwald, Stephen L.
, p. 15559 - 15563 (2016/12/09)
A method for the palladium-catalyzed fluorination of cyclic vinyl triflates has been developed. As with several previous palladium-catalyzed fluorination reactions using fluoride salts, controlling the regioselectivity presented a challenge in developing a practical synthetic procedure. The addition of triethyl(trifluoromethyl)silane (TESCF3) was found to effectively address this problem and resulted in drastically improved regioselectivities in this palladium-catalyzed fluorination reaction. This discovery, along with the use of a new biarylphosphine ligand, allowed for the development of an efficient and highly regioselective protocol for the fluorination of vinyl triflates. This method is compatible with a range of sensitive functional groups and provides access to five-, six-, and seven-membered cyclic vinyl fluorides.
Direct fluorination of styrenes
Shao, Qian,Huang, Yong
supporting information, p. 6584 - 6586 (2015/04/14)
We have developed a practical method to synthesize fluorostyrene compounds. A mild and regioselective mono-fluorination reaction occurred smoothly for various di- and trisubstituted styrenes in the presence of RuCl3 and N-fluorobenzenesulfonimide (NFSI). A tandem alkyne hydroarylation-olefin fluorination reaction was also developed using an Au catalyst.
Synthesis of monofluoroalkenes through selective hydrodefluorination of gem-difluoroalkenes with Red-Al
Wu, Jingjing,Xiao, Juan,Dai, Wenpeng,Cao, Song
, p. 34498 - 34501 (2015/04/27)
A novel and practical approach for the selective hydrodefluorination of gem-difluoroalkenes using Red-Al as a reductant at room temperature in CH2Cl2 without any additional base and metal catalyst was reported. Various monofluoroalkenes were obtained in moderate to high yields with good E-selectivity.
Metal-free, efficient oxyfluorination of olefins for the synthesis of α-fluoroketones
Yang, Qiang,Mao, Liu-Liang,Yang, Bin,Yang, Shang-Dong
supporting information, p. 3460 - 3463 (2014/07/21)
A novel oxyfluorination of olefin reactions has been developed. The reactions involve a metal-free and green catalytic system for the synthesis of α-fluoroketones which is an important building block for organic synthesis. Moreover, this reaction system exhibits great functional group tolerance.
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
1-tert-Butyl-1H-tetrazol-5-yl fluoromethyl sulfone (TBTSO2CH2F): A versatile fluoromethylidene synthon and its use in the synthesis of monofluorinated alkenes via JuliaKocienski olefination
Zhu, Lingui,Ni, Chuanfa,Zhao, Yanchuan,Ru, Jinbo
supporting information; experimental part, p. 5089 - 5100 (2010/08/20)
1-tert-Butyl-IH-tetrazol-5-yl fluoromethyl sulfone (TBTSO 2CI-12F) has been developed as a new and efficient fluoromethylidene synthon for the synthesis of both terminal and internal monofluoroalkenes via JuliaKocienski olefination reaction. The base-mediated reaction between TBTSO2CI-12F and carbonyl compounds (aldehydes and ketones) provided terminal monofluoroalkenes in good yields with moderate E!Z selectivity. The dominance of E- or Z-fluoroalkenes could be controlled by selection of proper reaction solvent and temperature. TBTSO 2CI-12F reagent was also found to be readily CL-alkylated, acylated, and phenylsulfonylated to give corresponding CL-functionalized fluorosulfones, which could be used in the synthesis of alkyl-, acyl-, and phenylsulfonyl-substituted internal monofluoroalkenes via JuliaKocienski olefination reactions.
Transformations of organic molecules with F-TEDA-BF4 in ionic liquid media
Pavlinac, Jasminka,Zupan, Marko,Stavber, Stojan
experimental part, p. 2394 - 2409 (2009/12/03)
The transformations of organic molecules with F-TEDA-BF4 (1) were investigated in the hydrophilic ionic liquid (IL) 1-butyl-3-methyl- imidazolium tetrafluoroborate ([bmim][BF4], 2) and the hydrophobic IL 1-butyl-3-methyl-imidazolium hexafluorophosphate ([bmim][PF6], 3). The range of substrates included alkyl substituted phenols 4a-c, 9, 13, 1,1-diphenylethene (15), alkyl aryl ketones 19-22, aldehydes 23-25 and methoxy-substituted benzene derivatives 26-30. The evaluation of the outcome of reactions performed in IL media in comparison to those of the corresponding reactions in conventional organic solvents revealed that the transformations in IL are less efficient and selective. The effect of the presence of a nucleophile (MeOH, H2O, MeCN) on the course of reaction was also studied.
