17715-70-7Relevant academic research and scientific papers
Acetyl Hypofluorite as a Taming Carrier of Elemental Fluorine for Novel Electrophilic Fluorination of Activated Aromatic Rings
Lerman, Ori,Tor, Yitzhak,Rozen, Shlomo
, p. 4629 - 4631 (1981)
The new fluorinating reagent CH3COOF, which is prepared in situ from F2, is used for electrophilic aromatic fluorinations of activated aromatic rings.
N-Halogeno compounds part 19: Electrophilic fluorinating agents of the multiple mono-N-fluoro class derived from nitrogen heterocycles
Banks, R. Eric,Besheesh, Mohamed K.,Mohialdin-Khaffaf, Suad N.,Sharif, Iqbal
, p. 157 - 161 (1997)
Bis(4-fluoro-1,4-diazoniabicyclo[2.2.2]oct-1-yl)-ethane and -propane tetratriflates (4, 5), and 1,1′-difluoro-4,4′-bipyridinium ditriflate (6) were prepared by solution-phase direct fluorination of bis(4-aza-1-azoniabicyclo[2.2.2]oct-1-yl)-ethane or -propane ditriflate (10, 11), and 4,4′-bipyridine respectively. The same technique was employed to convert the complex 4,4′-bipyridine · 2BF3 to the mono-NF derivative F3B-NC5H4-C5H4N+-F BF4- (7) and its monomethylated analogue (4-NC5H4)C5H4N+-CH3 TfO- to F-+ NC5H4-C5H4N+-CH3 (TfO- )2 (8). The results of site-specific electrophilic fluorination of some model substrates (1-morpholinocyclohexene, phenol, 2-naphthol, anisole, di-and tri-methoxybenzene) with 5, 7 and 8 are presented.
Multi-faceted reactivity of N-fluorobenzenesulfonimide (NFSI) under mechanochemical conditions: fluorination, fluorodemethylation, sulfonylation, and amidation reactions
Ardila-Fierro, Karen J.,Bari?i?, Dajana,Geneste, Hervé,Hernández, José G.
supporting information, p. 182 - 189 (2022/03/01)
In the search for versatile reagents compatible with mechanochemical techniques, in this work we studied the reactivity of N-fluorobenzenesulfonimide (NFSI) by ball milling. We corroborated that, by mechanochemistry, NFSI can engage in a variety of reactions such as fluorinations, fluorodemethylations, sulfonylations, and amidations. In comparison to the protocols reported in solution, the mechanochemical reactions were accomplished in the absence of solvents, in short reaction times, and in yields comparable to or higher than their solvent-based counterparts.
Shielding Effect of Micelle for Highly Effective and Selective Monofluorination of Indoles in Water
Bora, Pranjal P.,Bihani, Manisha,Plummer, Scott,Gallou, Fabrice,Handa, Sachin
, p. 3037 - 3042 (2019/04/01)
Highly selective direct monofluorination of indoles and arenes was developed through an approach that allows site-specific solubility of substrate and fluorine source in the micelle. This approach was highly selective for a broad range of substrates with excellent functional group tolerance. Differences in binding constant and solubility of indoles and arenes in the micelle allowed the fine-tuning of selectivity. Control experiments suggested a radical pathway and provided insight into the role of micelles of the environmentally benign amphiphile PS-750-M. Dynamic light scattering experiments strongly indicated the site-specific solubility of the substrate and fluorine source. The methodology was successfully adapted to gram scale, and the E-factor established from a recycle study indicated that the process is environmentally responsible and sustainable.
Pt(IV)-catalyzed generation and [4+2]-cycloaddition reactions of o-quinone methides
Radomkit, Suttipol,Sarnpitak, Pakornwit,Tummatorn, Jumreang,Batsomboon, Paratchata,Ruchirawat, Somsak,Ploypradith, Poonsakdi
supporting information; experimental part, p. 3904 - 3914 (2011/06/22)
Novel intermolecular and intramolecular generations of ortho-quinone methides and their formal [4+2]-cycloaddition reactions with olefins catalyzed by PtCl4 and AuCl3 under mild conditions have been developed. Good to excellent yields (up to 99%) and diastereoselectivity (up to >99:1) of the chromans were obtained. PtCl4 was found to be effective and compatible with various functional groups present in the substrates. A mechanism accounting for its catalytic cycle is proposed and discussed.
Transformations of organic molecules with F-TEDA-BF4 in ionic liquid media
Pavlinac, Jasminka,Zupan, Marko,Stavber, Stojan
experimental part, p. 2394 - 2409 (2009/12/03)
The transformations of organic molecules with F-TEDA-BF4 (1) were investigated in the hydrophilic ionic liquid (IL) 1-butyl-3-methyl- imidazolium tetrafluoroborate ([bmim][BF4], 2) and the hydrophobic IL 1-butyl-3-methyl-imidazolium hexafluorophosphate ([bmim][PF6], 3). The range of substrates included alkyl substituted phenols 4a-c, 9, 13, 1,1-diphenylethene (15), alkyl aryl ketones 19-22, aldehydes 23-25 and methoxy-substituted benzene derivatives 26-30. The evaluation of the outcome of reactions performed in IL media in comparison to those of the corresponding reactions in conventional organic solvents revealed that the transformations in IL are less efficient and selective. The effect of the presence of a nucleophile (MeOH, H2O, MeCN) on the course of reaction was also studied.
Solvent-free fluorination of organic compounds using N-F reagents
Stavber, Gaj,Zupan, Marko,Stavber, Stojan
, p. 2671 - 2673 (2008/02/03)
Efficient fluorination of 1,3-dicarbonyl compounds, enol acetates of aromatic ketones, and activated aromatic compounds was achieved under solvent-free conditions using Selectfluor F-TEDA-BF4 or Accufluor NFSi.
Efficient two-step synthesis of 9-aryl-6-hydroxy-3H-xanthen-3-one fluorophores
Bacci, James P.,Kearney, Aaron M.,Van Vranken, David L.
, p. 9051 - 9053 (2007/10/03)
A two-step method for the synthesis of 9-aryl-6-hydroxy-37f-xanthen-3-one fluorophores involving condensation of aryl aldehydes and fluororesorcinol is shown to proceed through a triarylmethane intermediate. The condensation is complicated by retro-Friede
Fluorinated xanthene derivatives
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, (2008/06/13)
The family of dyes of the invention are fluoresceins and rhodols that are directly substituted on one or more aromatic carbons by fluorine. These fluorine-substituted fluorescent dyes possess greater photostability and have lower sensitivity to pH changes in the physiological range of 6-8 than do non-fluorinated dyes, exhibit less quenching when conjugated to a substance, and possess additional advantages. The dyes of the invention are useful as detectable tracers and for preparing conjugates of organic and inorganic substances.
(3R,4S)-3-[4-(4-fluorophenyl)-4-hydroxypiperidin-1-yl]chroman-4,7-diol: A conformationally restricted analogue of the NRr2B subtype-selective NMDA antagonist (1S,2S)-1-(4-hydroxyphenyl)-2(4-hydroxy-4-phenylpiperidino)-1- propanol
Butler, Todd W.,Blake, James F.,Bordner, Jon,Butler, Paul,Chenard, Bertrand L.,Collins, Mary A.,DeCosta, Debra,Ducat, Mary J.,Eisenhard, Michael E.,Menniti, Frank S.,Pagnozzi, Martin J.,Sands, Steven B.,Segelstein, Barbara E.,Volberg, Walter,White, W. Frost,Zhao, Dayao
, p. 1172 - 1184 (2007/10/03)
(1S,2S)-1-(4-Hydroxyphenyl)-2-(4-hydroxy-4-phenylpiperidino)-1-propanol (CP-101,606, 1)is a recently described antagonist of N-methyl-D-aspartate (NUDA) receptors containing the NR2B subunit. In the present study, the optimal orientation of compounds of this structural type for their receptor was explored. Tethering of the pendent methyl group of 1 to the phenolic aromatic ring via an oxygen atom prevents rotation about the central portion of the molecule. Several of the new chromanol compounds have high affinity for the racemic [3H]CP-101,606 binding site on the NUDA receptor and protect against glutamate toxicity in cultured hippocampal neurons. The new ring caused a change in the stereochemical preference of the receptor - cis (erythro) compounds had better affinity for the receptor than the trans isomers. Computational studies suggest that steric interactions between the pendent methyl group and the phenol ring in the acyclic series determine which structures can best fit the receptor. The chromanol analogue, (3R,4S)- 3-[4-(4-fluorophenyl)-4-hydroxypiperidin-1-yl]chroman-4,7-diol (12a, CP- 283,097), was found to possess potency and selectivity comparable to CP- 101,606. Thus 12a is a new tool to explore the function of the NR2B- containing NUDA receptors.
