696-31-1Relevant academic research and scientific papers
Stereodivergent Alkyne Hydrofluorination Using Protic Tetrafluoroborates as Tunable Reagents
Geaneotes, Paul,Guo, Rui,Liu, Peng,Qi, Xiaotian,Wang, Ruihan,Wang, Yi-Ming,Xiang, Hengye
supporting information, p. 16651 - 16660 (2020/07/16)
The discovery of safe, general, and practical procedures to prepare vinyl fluorides from readily available precursors remains a synthetic challenge. The metal-free hydrofluorination of alkynes constitutes an attractive though elusive strategy for their preparation. Introduced here is an inexpensive and easily handled reagent that enables the development of simple and scalable protocols for the regioselective hydrofluorination of alkynes to access both the E and Z isomers of vinyl fluorides. These reaction conditions were suitable for a diverse collection of alkynes, including several highly functionalized pharmaceutical derivatives. Computational and experimental mechanistic studies support C?F bond formation through vinyl cation intermediates, with the E- and Z-hydrofluorination products forming under kinetic and thermodynamic control, respectively.
Chiral phosphoric acid catalyzed enantioselective [4 + 2] cycloaddition reaction of α-fluorostyrenes with imines
Terada, Masahiro,Kikuchi, Jun,Ye, Haiting
, p. 8957 - 8961 (2020/12/02)
An enantioselective [4 + 2] cycloaddition reaction of α-fluorostyrenes with N-benzoyl imines was demonstrated using a chiral phosphoric acid catalyst. Cycloaddition products having fluorine functionality were formed in high yields with excellent diastereo
A HF Loaded Lewis-Acidic Aluminium Chlorofluoride for Hydrofluorination Reactions
Kervarec, Ma?va-Charlotte,Kemnitz, Erhard,Scholz, Gudrun,Rudi?, Svemir,Braun, Thomas,J?ger, Christian,Michalchuk, Adam A. L.,Emmerling, Franziska
, p. 7314 - 7322 (2020/06/02)
The very strong Lewis acid aluminium chlorofluoride (ACF) was loaded with anhydrous HF. The interaction between the surface of the catalyst and HF was investigated using a variety of characterization methods, which revealed the formation of polyfluorides. Moreover, the reactivity of the HF-loaded ACF towards the hydrofluorination of alkynes was studied.
Gold-Catalyzed Hydrofluorination of Internal Alkynes Using Aqueous HF
Gauthier, Rapha?l,Mamone, Marius,Paquin, Jean-Fran?ois
supporting information, p. 9024 - 9027 (2019/11/14)
The gold-catalyzed hydrofluorination reaction of internal alkynes using hydrofluoric acid is reported. Notably, those conditions use one of the most economical sources of HF and are free of additional additives. Both symmetrical and unsymmetrical internal alkynes can be utilized, and the use of alkynes bearing a fluorinated group at the propargylic position as substrates allowed for a regioselective hydrofluorination reaction.
Design of fluorinated cyclopropane derivatives of 2-phenylcyclopropylmethylamine leading to identification of a selective serotonin 2C (5-HT2C) receptor agonist without 5-HT2B agonism
Cheng, Jianjun,Kozikowski, Alan P.,McCorvy, John D.,Roth, Bryan L.,Shen, Sida,Zhang, Guiping
, (2019/08/26)
A new series of fluorinated 5-HT2C agonists were designed and synthesized on the basis of our previous work on 2-phenylcyclopropylmethylamines as a potential approach for the treatment of central nervous system disorders. Key fluorinated cyclop
Selective Mono- And Dialkynylation of 1-Fluoro-2,2-diiodovinylarenes Using Pd-Catalyzed Decarboxylative Coupling Reactions
Jayaraman, Aravindan,Lee, Sunwoo
supporting information, p. 7923 - 7927 (2019/10/19)
Palladium-catalyzed decarboxylative coupling reactions using alkynoic acids and 1-fluoro-2,2-diiodovinylarenes provide mono- and dialkynylfluoroalkenes with high selectivity. When the reaction was conducted using DBU/DMSO, the hydrodeiodinated monoalkynyl
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.
(HETERO)ARYL CYCLOPROPYLAMINE COMPOUNDS AS LSD1 INHIBITORS
-
, (2013/05/09)
The invention relates to (hetero)aryl cyclopropylamine compounds, including particularly the compounds of formula (I) as described and defined herein, and their use in therapy, including, e.g., in the treatment or prevention of cancer, a neurological disease or condition, or a viral infection.
Expedient synthesis of α-substituted fluoroethenes
Mandal, Samir K.,Ghosh, Arun K.,Kumar, Rakesh,Zajc, Barbara
, p. 3164 - 3167 (2012/06/04)
A mild and efficient synthesis of 1-aryl-1-fluoroethenes from benzothiazolyl (aryl)fluoromethyl sulfones and paraformaldehyde, under DBU- or Cs2CO3-mediated conditions at room temperature, is described. A comparable diethyl fluoro(naphthalen-2-yl)methylphosphonate reagent does not react with paraformaldehyde under these mild conditions. The utility of the methodology for synthesis of terminal α-fluoroalkenes bearing electron-withdrawing functionalities is also shown.
