703-17-3Relevant academic research and scientific papers
Bench-Stable Electrophilic Fluorinating Reagents for Highly Selective Mono- and Difluorination of Silyl Enol Ethers
Adachi, Akiya,Aikawa, Kohsuke,Ishibashi, Yuichiro,Nozaki, Kyoko,Okazoe, Takashi
supporting information, p. 11919 - 11925 (2021/07/02)
Efficient methods for the synthesis of fluorinated compounds have been intensively studied, recently. Development of practical fluorinating reagents is indispensable for this purpose. Herein, bench-stable electrophilic fluorinating reagents were synthesized as N-fluorobenzenesulfonimide (NFSI) substitutes. Reagents obtained by replacing one of the NFSI sulfonyl groups with an acyl group led to the highly selective monofluorination of silyl enol ethers with suppression of undesired overreaction, that is, difluorination. On the other hand, reagents bearing electron-withdrawing substituents at NFSI benzenesulfonyl groups efficiently facilitated the difluorination of silyl enol ethers under base-free conditions. Thus, both mono- and difluorinated target materials were prepared from the same substrate.
REACTIVE EXTRACTION OF WATER
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Paragraph 0073-0076, (2020/04/09)
Described herein are methods and compounds for extracting water from an aqueous solution. For example, some embodiments include method for extracting water from an aqueous solution, comprising contacting the aqueous solution with a compound comprising one or more carbonyl moieties having an equilibrium constant for a hydration of the carbonyl moiety of at least about 0.5; separating a composition comprising the hydrated compound from the aqueous solution; and reacting the hydrated compound to obtain water.
Practical Access to Difluoromethyl Ketones via Straightforward Decarboxylative Difluorination of β-Ketoacids
Li, Yin-Long,Li, Jian,Deng, Jun
, p. 1407 - 1412 (2017/04/18)
A facile synthetic approach to a series of difluoromethyl ketones from β-ketoacids has been described. This transformation is achieved through the straightforward decarboxylative difluorination of β-ketoacids in the absence of any catalyst. Furthermore, the resulted difluoromethyl ketones can be easily converted into corresponding difluoromethylated building blocks for pharmaceuticals and materials. (Figure presented.).
A Practical Synthesis of α-Fluoroketones in Aqueous Media by Decarboxylative Fluorination of β-Ketoacids
Li, Jian,Li, Yin-Long,Jin, Nan,Ma, Ai-Lun,Huang, Ya-Nan,Deng, Jun
supporting information, p. 2474 - 2478 (2015/08/18)
A practical and novel process for the decarboxylative fluorination of β-ketoacids in water in the presence of phase transfer catalyst has been developed, affording a series of α-fluoroketones in good to excellent yields. Furthermore, a preliminary investigation for the catalytic asymmetric transformation was performed and a proposed mechanistic pathway for this catalytic process was proposed.
Difluorohomologation of ketones
Kosobokov, Mikhail D.,Levin, Vitalij V.,Struchkova, Marina I.,Dilman, Alexander D.
supporting information, p. 760 - 763 (2015/03/05)
A method for the homologation of ketones with the CF2 fragment is described. The reaction involves silylation, room-temperature difluorocyclopropanation of silyl enol ethers, and selective ring opening of cyclopropanes under acidic conditions. The whole three-step sequence is conveniently performed in a one-pot mode.
The use of fluoride as a leaving group: SN2′ displacement of a C-F bond on 3,3-difluoropropenes with organolithium reagents to give direct access to monofluoroalkenes
Bergeron, Maxime,Johnson, Thomas,Paquin, Jean-Francois
supporting information; experimental part, p. 11112 - 11116 (2012/02/02)
Lithium is the key to activate the nucleofuge ability of fluoride in the title transformation (see scheme). This simple and straightforward approach not only provides a practical synthetic method for the preparation of monofluoroalkenes, an important fluo
Reactions of enamines with selectfluor: A straightforward route to difluorinated carbonyl compounds
Peng, Weimin,Shreeve, Jean'ne M.
, p. 5760 - 5763 (2007/10/03)
Reactions of enamines, preformed from β-dicarbonyl and monocarbonyl compounds, with Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2] octane bis(tetrafluoroborate) under mild conditions (triethylamine (TEA) or molecular sieves) easily led to the corresponding difluorinated carbonyl compounds in high yields.
N-Fluoro-bis[(trifluoromethyl)sulfonyl]imide: Electrophilic fluorination of imines and some methyl-substituted pyridines
Ying,DesMarteau,Gotoh
, p. 15 - 22 (2007/10/02)
Direct fluorination of imines with N-fluoro-bis[(trifluoromethyl)sulfonyl]imide 1 afforded mono and/or difluoroketones without the need of a strong base to first generate the imine anions. Structurally related 2- and 4-methyl-substituted pyridines gave the respective fluoromethyl pyridines with 1. Our results suggest that an enamine intermediate plays a key role in these reactions.
SELECTIVE MONO- AND DIFLUORINATION OF ENOLATES
Differding, Edmond,Rueegg, Gabriela M.,Lang, Robert W.
, p. 1779 - 1782 (2007/10/02)
The selective transformation of enolates into mono- and difluorinated carbonyl compounds can be performed in a one-pot procedure using N-F-sultam 1.The yields and the selectivity of the fluorination strongly depend on the counterion of the enolate and the acidity of the protons α to the carbonyl group.
