308-27-0Relevant academic research and scientific papers
Enantioselective NHC-Catalyzed Redox [2+2] Cycloadditions with Perfluoroketones: A Route to Fluorinated Oxetanes
Davies, Alyn T.,Slawin, Alexandra M. Z.,Smith, Andrew D.
supporting information, p. 18944 - 18948 (2016/01/26)
The N-heterocyclic carbene (NHC) catalyzed redox formal [2+2] cycloaddition between α-aroyloxyaldehydes and perfluoroketones, followed by ring-opening in situ delivers a variety of perfluorinated β-hydroxycarbonyl compounds in good yield, and excellent diastereo- and enantioselectivity. Through a reductive work-up and subsequent cyclization, this protocol offers access to highly substituted fluorinated oxetanes in two steps and in high ee.
Approaches to prepare perfluoroalkyl and pentafluorophenyl copper couples for cross-coupling reactions with organohalogen compounds
Kremlev, Mikhail M.,Mushta, Aleksej I.,Tyrra, Wieland,Yagupolskii, Yurii L.,Naumann, Dieter,Sch?fer, Mathias
, p. 19693 - 19699 (2015/11/27)
The reactions of iodoperfluoroalkanes CnF2n+1I (n = 2, 3, 4) and n-BuLi at low temperatures give NMR spectroscopic evidence for LiCnF2n+1 which were converted into LiCu(CnF2n+1)2 derivatives upon treatment with 0.5 mol copper(i) bromide, CuBr. An alternative route to obtain perfluoroorgano copper couples, Cu(Rf)2Ag (Rf = n-C3F7, n-C4F9, C6F5) was achieved from the reactions of the corresponding perfluoroorgano silver(i) reagents, AgRf, and elemental copper through redox transmetallations. The composition of the resulting reactive intermediates was investigated by means of 19F NMR spectroscopy and ESI mass spectrometry. Perfluoro-n-propyl and perfluoro-n-butyl copper-silver reagents prepared by the oxidative transmetallation route exhibited good properties in C-C bond formation reactions with acid chlorides even under moderate conditions. Substitution of bromine directly bound to aromatics for perfluoroalkyl groups was achieved at elevated temperatures, while success in halide substitution reactions using lithium copper couples remained poor.
A new entry for the oxidation of fluoroalkyl-substituted methanol derivatives: Scope and limitation of the organoiodine(V) reagent-catalyzed oxidation
Tanaka, Yusuke,Ishihara, Takashi,Konno, Tsutomu
experimental part, p. 99 - 104 (2012/05/07)
Oxidation of various fluoroalkyl-substituted methanol derivatives under the influence of a catalytic amount of sodium 2-iodobenzenesulfonate and Oxone in CH3CN or CH3NO2 was investigated in detail. The efficiency of the newly developed oxidation was also evaluated by comparison to other oxidations, such as Dess-Martin, PDC, and Swern oxidation.
Sequential perfluoroalkylation and asymmetric reduction of nitriles triggered with perfluoroalkyl titanates: catalytic asymmetric synthesis of perfluoroalkyl amines
Mikami, Koichi,Murase, Tatsushi,Zhai, Lili,Kawauchi, Susumu,Itoh, Yoshimitsu,Ito, Shigekazu
scheme or table, p. 1371 - 1373 (2010/05/19)
Highly enantio-enriched perfluoroalkyl amines are shown to be synthesized by perfluoroalkylation and asymmetric reduction of nitriles. Perfluoroalkylation of nitriles can be attained by the Lewis acidic perfluoroalkyl titanate reagents to give acyclic ket
The reaction of carboxylic acid esters with RfMgBr: A convenient synthesis of perfluoroalkyl ketones
Xue, Can,He, Guangke,Fu, Chunling,Xue, Liqin,Lin, Zhenyang,Ma, Shengming
experimental part, p. 7012 - 7019 (2011/02/26)
An efficient method for the preparation of the synthetically attractive perfluoroalkyl ketones through the reaction of readily available alkenoates, alkynoates, or regular carboxylic esters with perfluoroalkyl Grignard reagents at -70 to -60 °C in diethyl
