56874-95-4Relevant academic research and scientific papers
A new synthesis of 2-fluoro-1-naphthols
Cai, Xiaohong,Wu, Kai,Dolbier Jr., William R.
, p. 479 - 482 (2005)
A general synthesis of 2-fluoro-1-naphthols in two steps from 1-indanones is reported. The 1-indanones are first converted to difluoromethyl 2-fluoro-1-napthyl ethers by reaction with difluorocarbene source, trimethylsilyl 2-fluorosulfonyl-2,2-difluoroacetate (TFDA). These ethers are then converted in high yield to the respective naphthols by heating with a mixture of acetic acid and 48% HBr.
Decarboxylative Fluorination of Arylcarboxylic Acids Promoted by ortho-Hydroxy and Amino Groups
Wang, Dinghai,Yuan, Zheliang,Liu, Qilun,Chen, Pinhong,Liu, Guosheng
, p. 507 - 514 (2018/04/25)
A novel decarboxylative fluorination process has been developed for the synthesis of ortho-hydroxy/amino arylfluorides from salicylic acid analogs, in which the ortho-hydroxy/amino group plays an important role in the transformation. In addition, various arylfluorides are obtained in good to excellent yields under mild conditions.
SelectfluorTMon a PolyHIPE Material as Regenerative and Reusable Polymer-Supported Electrophilic Fluorinating Agent
Kawada, Kosuke,Okano, Koji,Iskra, Jernej,Krajnc, Peter,Cahard, Dominique
supporting information, p. 584 - 589 (2017/02/23)
The first recyclable polymer-supported electrophilic fluorinating agent was prepared by reaction of molecular fluorine with the triethylenediamine motif that is grafted onto a poly(4-vinylbenzyl chloride-co-divinylbenzene) polyHIPE material. The resulting
Promotional effect of ionic liquids in the electrophilic fluorination of phenols
Borodkin, Gennady I.,Elanov, Innokenty R.,Shubin, Vyacheslav G.
, p. 60 - 71 (2018/02/07)
The influence of a stoichiometric amount of ionic liquids (IL) on the fluorination of phenols in various solvents has been studied. The fluorination of phenol, 1-naphthol and resorcinol was carried out using 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (F-TEDA-BF4, Selectfluor) with the formation of 2-fluoro-, 4-fluorophenol, 2-fluoro-, 4-fluoronaphthol and 4-fluoro-, 4,6-difluoro-benzene-1,3-diol as the main products. The use of a stoichiometric amount of ionic liquid as an additive results in acceleration of the reactions. The effect is most significant at low temperatures. It has been found that solvent polarity has an essential effect on the difference in yields of fluoroproducts obtained in the presence of IL and without it.
A direct catalytic ring expansion approach to o-fluoronaphthols and o/p-fluorophenols from indanones and 2-cyclopentenones
Chang, Jian,Song, Xiaoning,Huang, Wanqiao,Zhu, Dongsheng,Wang, Mang
supporting information, p. 15362 - 15365 (2015/10/20)
A direct method for the synthesis of o-fluoronaphthols and o/p-fluorophenols has been developed by a catalytic ring expansion of indanones and 2-cyclopentenones, in which TMSCF2Br was used as a unique:CF2 source, a TMS transfer agent, as well as the Br- and F- releaser for the enolization, difluorocyclopropanation, desilylation, ring opening, defluorination, and aromatization sequence.
Selective C-H bond fluorination of phenols with a removable directing group: Late-stage fluorination of 2-phenoxyl nicotinate derivatives
Lou, Shao-Jie,Chen, Qi,Wang, Yi-Feng,Xu, Dan-Qian,Du, Xiao-Hua,He, Jiang-Qi,Mao, Yang-Jie,Xu, Zhen-Yuan
, p. 2846 - 2849 (2015/05/20)
A facile and site-selective C-H bond fluorination of phenols using removable 2-pyridyloxy group as an auxiliary was developed. Alternatively, late-stage C-H bond fluorination of bioactive 2-phenoxyl nicotinate derivatives and diflufenican were also feasible under the present strategy.
Fluorination of aromatic compounds with N-fluorobenzenesulfonimide under solvent-free conditions
Andreev,Borodkin,Shubin
scheme or table, p. 1468 - 1473 (2010/03/24)
Reactions of N-fluorobenzenesulfonimide with methylbenzenes, phenols, and phenol ethers were studied under solvent-free conditions. The rate constant ratio for the reactions with mesitylene and durene indicates polar mechanism of the process. Solvent-free fluorination of aromatic compounds with N-fluorobenzenesulfonimide in some cases is more selective than reactions with other N-F reagents in a solvent.
N-halogeno compounds. Part 18. 1-Alkyl-4-fluoro-1,4-diazoniabicyclo [2.2.2] octane salts: User-friendly site-selective electrophilic fluorinating agents of the N-fluoroammonium class
Banks, R. Eric,Besheesh, Mohamed K.,Mohialdin-Khaffaf, Suad N.,Sharif, Iqbal
, p. 2069 - 2076 (2007/10/03)
Methods of synthesis are described for a range of 1-alkyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts [R-N+(CH2CH2)3N+-F (X-)2, where R = CH3, CH2Cl, C2H5, CF3CH2, C8H17 and (X-)2 = (TfO-)2, (BF4-)2, (PF6-)2, (TfO-, BF4-), (TfO-, PF6-), (TfO-, FSO3-)] by direct fluorination (with neat F2 at ≤20 mmHg or F2-N2 blends at 1 atm pressure) of monoquaternary salts of 1,4-diazabicyclo[2.2.2]octane [R-+N(CH2CH2)3N X-] or their 1:1 adducts with boron trifluoride, phosphorus pentafluoride, or sulfur trioxide in acetonitrile at ca - 35°C. The results of site-selective electrophilic fluorination of diethyl sodio(phenyl)malonate [→ PhCF(CO2Et)2], 1-morpholinocyclohexene (→ 2-fluorocyclohexanone), phenol (→ 2- and 4-FC6H4OH), 1- and 2-hydroxynaphthalene (→ 2- and 4-FC10H6OH, and 1-FC10H6OH and 1,1-difluoro-2-oxo-1,2-dihydronaphthalene, respectively), acetanilide (→ 2- and 4-FC6H4NHCOCH3), anisole (→ 2- and 4-FC6H4OCH3) and sodium benzenesulfinate (→ PhSO2F) with these N-fluoroammonium salts are presented.
Selective and efficient direct fluorination of polycyclic aromatic hydrocarbons using 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)
Stavber, Stojan,Zupan, Marko
, p. 1077 - 1078 (2007/10/03)
A new N-F fluorinating reagent 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Accufluor NFTh) was effectively used for selective fluorination of polycyclic aromatics. Naphthalene was site-selectively fluorinated to 1-fluoronaphthalene, phenanthrene to 9-fluorophenanthrene, and pyrene to 1-fluoropyrene. In a series of substituted naphthalenes the regioselectivity and effectiveness of fluorination depended on the position and the nature of the substituents.
Chemistry of Organo Halogenic Molecules. 140. Role of the Reagent Structure on the Transformations of Hydroxy Substituted Organic Molecules with the N-Fluoro Class of Fluorinating Reagents
Zupan, Marko,Iskra, Jernej,Stavber, Stojan
, p. 1655 - 1660 (2007/10/02)
Hydroxy-substituted organic molecules were used as target molecules in investigations of the role of the reagent structure on the reactivity of three types of N-F class fluorinating reagents: 1-chloromethyl-4-fluoro-1,4-diazoniabicyclooctane bis(tetrafluoroborate) F-TEDA (1a), N-fluorobis(phenylsulfonyl)amine NSF (1b), and N-Fluoropyridinium heptafluorodiborate-pyridine (1/1) NFP (1c).Methanol is stable, but hydroquinone is very quickly transformed in acetonitrile to quinone with F-TEDA at room temperature: on the other hand, NSF is less reactive, while oxidation with NFP is achieved only at an elevated temperature; a structure variation of the hydroquinone derivatives did not influence oxidation.Fluorination was achieved with monohydroxy-substituted aromatic compounds; a similar trend concerning the reactivity of N-F reagent (1) was also observed in reactions with 1- and 2-naphthol, while 9-phenanthrol gave 10,10-difluoro-9-(10H)-phenanthrenone with F-TEDA in acetonitrile and 9,10-phenanthrenequinone with NSF.Dealkylation was observed in a reaction with 4-methoxyphenol; although the thio analogue gave bis(4-methoxyphenyl) disulfide, the reactivity was changed and NSF was more reactive than F-TEDA and NFP.
