2932-58-3Relevant articles and documents
Synthesis of [18 F]-γ-Fluoro-α,β-unsaturated Esters and Ketones via Vinylogous 18 F-Fluorination of α-Diazoacetates with [18 F]AgF
Brooks, Allen F.,Ichiishi, Naoko,Jackson, Isaac M.,Lee, So Jeong,Sanford, Melanie S.,Scott, Peter J. H.,Thompson, Stephen
supporting information, p. 4401 - 4407 (2019/11/21)
This communication reports a method for the vinylogous radiofluorination of α-diazoacetates to generate [18 F]-γ-fluoro-α,β-unsaturated esters and ketones in moderate to good radiochemical yields. The method uses no-carrier-added [18 F]AgF and is compatible with aromatic and non-aromatic substrates and a number of different functional groups. The labeling method is showcased in the synthesis of a fluorinated cholest-5-en-3-one derivative as well as a difluorinated product pertinent to drug discovery.
TRIAZOLOPYRIDINE ETHER DERIVATIVES AND THEIR USE IN NEUROLOGICAL AND PYSCHIATRIC DISORDERS
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Page/Page column 62-63, (2015/04/15)
The disclosure generally relates to compounds of formula I, including their salts, as well as compositions and methods of using the compounds. The compounds modulate the mGluR2 receptor and may be useful for the treatment of various disorders of the central nervous system.
β-fluoroamphetamines via the stereoselective synthesis of benzylic fluorides
Cresswell, Alexander J.,Davies, Stephen G.,Lee, James A.,Roberts, Paul M.,Russell, Angela J.,Thomson, James E.,Tyte, Melloney J.
supporting information; experimental part, p. 2936 - 2939 (2010/09/10)
A range of substituted aryl epoxides undergo efficient ring-opening hydrofluorination upon treatment with 0.33 equiv of BF3-OEt 2 in CH2Cl2 at -20 -°C to give the corresponding syn-fluorohydrins, consistent with a mechanism involving a stereoselective SN1-type epoxide ring-opening process. The benzylic fluoride products of these reactions are valuable templates for further elaboration, as demonstrated by the preparation of a range of aryl-substituted β-fluoroamphetamines.
Fluorination with ionic liquid EMIMF(HF)2.3 as mild HF source
Yoshino, Hideaki,Matsumoto, Kazuhiko,Hagiwara, Rika,Ito, Yasuhiko,Oshima, Koichiro,Matsubara, Seijiro
, p. 29 - 35 (2007/10/03)
Hydrogen fluoride is a basic fluorinating reagent, but handling it is difficult. For this reason, some modified fluorinating reagents such as HF-pyridine, Et3N-HF, and poly(hydrogen fluoride) complex have been developed. Those reagents, however, still require aqueous work-up procedures which generate hydrogen fluoride. Recently, ionic liquids have received much attention because of the ease in handling them and the possibility of non-aqueous work-up. An ionic liquid, 3-ethyl-1-methyimidazolium oligo hydrogen fluoride (EMIMF(HF)2.3), which is stable in air and moisture, can be used as a hydrogen fluoride equivalent for some fluorination reactions; it does not require an aqueous work-up.
Boron trifluoride-induced reactions of phenylglycidyl ethers: A convenient synthesis of enantiopure, stereodefined fluorohydrins
Islas-González, Gabriela,Puigjaner, Cristina,Vidal-Ferran, Anton,Moyano, Albert,Riera, Antoni,Pericàs, Miquel A.
, p. 6337 - 6341 (2007/10/03)
Ring-opening hydrofluorination of enantiomerically pure (2S,3S)-3-arylglycidyl ethers (aryl=phenyl, 4-trifluoromethylphenyl) by boron trifluoride-diethyl ether under mild conditions provides β-fluoro alcohols in good yield in a stereospecific manner with
A mild ring opening fluorination of epoxide with ionic liquid 1-ethyl-3-methylimidazorium oligo hydrogenfluoride (EMIMF(HF) 2.3)
Yoshino, Hideaki,Nomura, Kenichi,Matsubara, Seijiro,Oshima, Koichiro,Matsumoto, Kazuhiko,Hagiwara, Rika,Ito, Yasuhiko
, p. 1127 - 1129 (2007/10/03)
Ring opening fluorination of epoxides with hydrogen fluoride in ionic liquid 1-ethyl-3-methylimidazorium oligo hydrogenfluoride EMIMF(HF)2.3 was demonstrated. This ionic liquid released hydrogen fluoride graduately to make mild conditions witho
Process for the production of fluorinated organic compounds and fluorinating agents
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, (2008/06/13)
A process for the production of a fluorinated organic compound, characterized by fluorinating an organic compound having a hydrogen atoms using IF5; and a novel fluorination process for fluorinating an organic compound having a hydrogen atoms by using a fluorinating agent containing IF5 and at least one member selected from the group consisting of acids, bases, salts and additives.
Regioselective synthesis of fluorohydrines via SN2-type ring-opening of epoxides with TBABF-KHF2
Akiyama, Yuriko,Fukuhara, Tsuyoshi,Hara, Shoji
, p. 1530 - 1532 (2007/10/03)
We found that the ring-opening fluorination of terminal epoxides using TBABF-KHF2 proceeds with high selectivity through the SN2 mechanism. As TBABF-KHF2 is easily obtainable, is stable, and can be used in glassware, it ca
Regioselective, stereospecific, and chemoselective fluorination of epoxy alcohols: Development of fluorinating hybrid reagents, associated with Lewis acid metal fluoride/ammonium hydrogen fluoride
Mikami, Koichi,Ohba, Shiho,Ohmura, Hirofumi
, p. 77 - 82 (2007/10/03)
A new type of fluorinating reagent of Lewis acid metal fluoride/ammonium hydrogen fluoride is developed for regio-, stereo-, and chemoselective ring opening fluorination of epoxy alcohols.
Enantioselective ring-opening of epoxides by HF-reagents: Asymmetric synthesis of fluoro lactones
Haufe, Günter,Bruns, Stefan,Runge, Martina
, p. 55 - 61 (2007/10/03)
The asymmetric ring opening of meso- and racemic-epoxides with different HF-reagents mediated by enantiopure (salen)chromium chloride provides optically active fluorohydrins with maximum 90% e.e. This reaction as well as lipase-catalyzed deracemization of
