66472-51-3Relevant academic research and scientific papers
Gold N-Heterocyclic Carbene Catalysts for the Hydrofluorination of Alkynes Using Hydrofluoric Acid: Reaction Scope, Mechanistic Studies and the Tracking of Elusive Intermediates
Bédard, Sandrine,Cavallo, Luigi,Falivene, Laura,Gauthier, Rapha?l,Nolan, Steven P.,Paquin, Jean-Fran?ois,Saab, Marina,Tzouras, Nikolaos V.,Van Hecke, Kristof,Zhang, Ziyun
, (2021/12/09)
An efficient and chemoselective methodology deploying gold-N-heterocyclic carbene (NHC) complexes as catalysts in the hydrofluorination of terminal alkynes using aqueous HF has been developed. Mechanistic studies shed light on an in situ generated catalyst, formed by the reaction of Br?nsted basic gold pre-catalysts with HF in water, which exhibits the highest reactivity and chemoselectivity. The catalytic system has a wide alkyl substituted-substrate scope, and stoichiometric as well as catalytic reactions with tailor-designed gold pre-catalysts enable the identification of various gold species involved along the catalytic cycle. Computational studies aid in understanding the chemoselectivity observed through examination of key mechanistic steps for phosphine- and NHC-coordinated gold species bearing the triflate counterion and the elusive key complex bearing a bifluoride counterion.
Fluorinated cyclopropanes: Synthesis and chemistry of the aryl α,β,β-trifluorocyclopropane motif
Thomson, Connor J.,Zhang, Qingzhi,Al-Maharik, Nawaf,Bühl, Michael,Cordes, David B.,Slawin, Alexandra M. Z.,O'Hagan, David
, p. 8415 - 8418 (2018/08/04)
A general route to aryl α,β,β-trifluorocyclopropanes is reported and aryl oxidation gave the corresponding α,β,β-trifluorocyclopropane carboxylic acid. Reactions of the corresponding amides with phenol/thiophenol resulted in HF elimination and then conjugate addition. The partially fluorinated cyclopropane has a similar lipophilicity to -CF3 despite three carbon atoms, and it emerges as a novel motif for drug discovery.
Designer HF-Based fluorination reagent: Highly regioselective synthesis of fluoroalkenes and gem -difluoromethylene compounds from alkynes
Okoromoba, Otome E.,Han, Junbin,Hammond, Gerald B.,Xu, Bo
supporting information, p. 14381 - 14384 (2015/01/09)
Hydrogen fluoride (HF) and selected nonbasic and weakly coordinating (toward cationic metal) hydrogen-bond acceptors (e.g., DMPU) can form stable complexes through hydrogen bonding. The DMPU/HF complex is a new nucleophilic fluorination reagent that has high acidity and is compatible with cationic metal catalysts. The gold-catalyzed mono- and dihydrofluorination of alkynes using the DMPU/HF complex yields synthetically important fluoroalkenes and gem-difluoromethlylene compounds regioselectively.
Preparation of fluoroalkenes via the Shapiro reaction: Direct access to fluorinated peptidomimetics
Yang, Ming-Hsiu,Matikonda, Siddharth S.,Altman, Ryan A.
supporting information, p. 3894 - 3897 (2013/09/02)
Fluoroalkenes represent a useful class of peptidomimetics with distinct biophysical properties. Current preparations of this functional group commonly provide mixtures of E- or Z-fluoroalkene diastereomers, and/or mixtures of nonfluorinated products. To directly access fluoroalkenes in good stereoselectivity, a Shapiro fluorination reaction was developed. Fluoroalkene products were accessed in one- or two-step sequences from widely available ketones. This strategy should be useful for the preparation of fluorinated analogs of peptide-based therapeutics, many of which would be challenging to prepare by alternate strategies.
Grignard cross-coupling amenable to large scale production of α-fluorostyryl and α-fluorovinylthiophenes
Qiu, Jian,Gyorokos, Albert,Tarasow, Theodore M.,Guiles, Joseph
supporting information; experimental part, p. 9775 - 9777 (2009/04/06)
(Chemical Equation Presented) An efficient nickel-catalyzed Kumada-Corriu cross coupling enabled the introduction of an α-fluorovinyl functionality with excellent conversion and specificity.
Fluorinated phenylcyclopropylamines. Part 5: Effects of electron-withdrawing or -donating aryl substituents on the inhibition of monoamine oxidases A and B by 2-aryl-2-fluoro-cyclopropylamines
Hruschka, Svenja,Rosen, Thomas C.,Yoshida, Shinichi,Kirk, Kenneth L.,Froehlich, Roland,Wibbeling, Birgit,Haufe, Guenter
, p. 7148 - 7166 (2008/12/22)
A series of racemic, diastereoisomeric aryl cyclopropylamines substituted with fluorine in the 2-position and electron-donating and electron-withdrawing groups on the aromatic ring have been prepared. These represent analogues of the classic MAO inhibitor
2,2-Difluoro-1,3-dimethylimidazolidine (DFI). A new fluorinating agent
Hayashi, Hidetoshi,Sonoda, Hiroshi,Fukumura, Kouki,Nagata, Teruyuki
, p. 1618 - 1619 (2007/10/03)
2,2-Difluoro-1,3-dimethylimidazolidine (DFI) is a new deoxo-fluorinating agent that is useful for the conversion of alcohols to monofluorides, and aldehydes/ketones to gem-difluorides under mild conditions.
Process for the preparation of α-flurostyrene
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, (2008/06/13)
Process for the preparation of α-fluorostyrene from fluoroolefins: STR1 Z=hydrogen, fluorine, chlorine X=iodine, bromine, chlorine. A halogenated aromatic (I) is reacted with a fluorine-substituted ethylene (II) in the presence of a palladium catalyst to
