1-Fluoro-2,4,6-trichloro-1,3,5-triazinium tetrafluoroborate: synthesis, characterization, and ability to effect electrophilic aromatic substitution

Banks, R. E.; Besheesh, Mohamed K.; Fraenk, Wolfgang; Klapötke, Thomas M.

doi:10.1016/j.jfluchem.2003.08.010

Cited by 11 publications

(5 citation statements)

References 13 publications

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“…These data suggest weak dependence of the regioselectivity on the nature of N-F reagent and polarity of the medium provided that specific effects are absent. The reverse ortho/para-isomer ratios were reported, e.g., for the fluorination with F-TEDA-BF 4 in strongly acidic medium (CF 3 SO 3 H, 0.8) [35] and with 2,4,6-trichloro-1-fluoro-1,3,5-triazinium tetrafluoroborate in nitromethane (0.5) [36]. Presumably, in the first case the reactive species is protonated trifluoromethanesulfonyl hypofluorite SF 3 SO 2 OHF + rather than F-TEDA-BF 4 [35], while in the second steric interaction between the methoxy group in the substrate and chlorine atoms in the reagent could hinder attack by the latter on the ortho position.…”

Section: Fluorination Of Aromatic Compounds With N-fluorobenzenesulfomentioning

confidence: 85%

Fluorination of aromatic compounds with N-fluorobenzenesulfonimide under solvent-free conditions

2009

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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.Fluorinated aromatic compounds are widely used as pesticides, medicinal agents, and various functional materials; therefore, development of ecologically friendly and selective fluorination procedures seems to be an important problem [1][2][3]. During the past two decades, N-F reagents [1-17] have been extensively used as source of fluorine in mild and selective fluorination of organic compounds. In particular, such reagent is N-fluorobenzenesulfonimide (NFSI) [2,4,[7][8][9][18][19][20][21][22][23][24]. It is nonhygroscopic, stable to storage, and convenient to handle with. N-Fluorobenzenesulfonimide is quite reactive, but at the same time it exhibits a moderate oxidative ability [2], which is important for fluorination of organic compounds with low oxidation potentials. N-Fluorobenzenesulfonimide is commonly used to effect fluorination of carbanions, enolates, and enol ethers in the synthesis of fluorinated intermediate products necessary for the manufacture of medicinal agents [7][8][9]. Direct fluorination of aromatic compounds with NFSI was performed less frequently than with other N-F reagents, e.g., 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts .The goal of the present work was to study the selectivity in fluorination of aromatic compounds, namely methyl-substituted benzenes, phenols, and phenol ethers, with NFSI in the absence of a solvent. The selectivity problem in electrophilic fluorination under these conditions remains poorly studied (cf. [22]).We have found that the yield of monofluoro derivatives in the fluorination of polymethylbenzenes

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Section: Fluorination Of Aromatic Compounds With N-fluorobenzenesulfomentioning

confidence: 85%

Fluorination of aromatic compounds with N-fluorobenzenesulfonimide under solvent-free conditions

2009

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“…In 2003, Banks et al reported the synthesis of N -fluoro-2,4,6-trichloro-1,3,5-triazinium tetrafluoroborate ( 32-2 ) and its fluorination of aromatic compounds [ 100 ]. Although the syntheses of N -fluoro-2,4,6-trifluoro-1,3,5-triazinium hexafluoroarsenate and N -fluoro-2,4,6-trichloro-1,3,5-triazinium hexafluoroarsenate had been reported a decade earlier (1993) [ 101 ], their fluorination ability had not been disclosed.…”

Section: Reviewmentioning

confidence: 99%

Development of N-F fluorinating agents and their fluorinations: Historical perspective

Umemoto¹,

Yang²,

Hammond³

2021

Beilstein J. Org. Chem.

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This review deals with the historical development of all N-F fluorinating agents developed so far. The unique properties of fluorine make fluorinated organic compounds attractive in many research areas and therefore fluorinating agents are important. N-F agents have proven useful by virtue of their easy handling. This reagent class includes many types of N-F compounds: perfluoro-N-fluoropiperidine, N-fluoro-2-pyridone, N-fluoro-N-alkylarenesulfonamides, N-fluoropyridinium salts and derivatives, N-fluoroquinuclidium salts, N-fluoro-trifluoromethanesulfonimide, N-fluoro-sultams, N-fluoro-benzothiazole dioxides, N-fluoro-lactams, N-fluoro-o-benzenedisulfonimide, N-fluoro-benzenesulfonimide, 1-alkyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts, N-fluoropyridinium-2-sulfonate derivatives, 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane salts, N-fluorodinitroimidazole, N-fluoro-trichloro-1,3,5-triazinium salt, N-F ethano-Tröger’s base derivatives, N-fluoro-methanesulfonimide, N-fluoro-N-arylarenesulfonamides, bisN-F salts such as N,N’-difluorobipyridinium salts and N,N’-difluoro-1,4-diazoniabicyclo[2.2.2]octane salts, and their many derivatives and analogs, including chiral N-F reagents such as optically active N-fluoro-sultam derivatives, N-fluoro-alkaloid derivatives, DABCO-based N-F derivatives, and N-F binaphthyldisulfonimides. The synthesis and reactions of these reagents are described chronologically and the review also discusses the relative fluorination power of each reagent and their mechanisms chronicling developments from a historical perspective.

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“…Several methods have been reported for fluorination of organic compounds [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20]. Although the direct fluorination by elemental fluorine has been investigated by several researchers [2], there are still some problems with the fluorine radical.…”

Section: Introductionmentioning

confidence: 99%

“…Electron withdrawing effects of fluorine and presence of an excellent leaving group adjacent to fluorine is a common character of these reagents. The best reagents in this category include 1-fluoro-substituted 1,4-diazoniabicyclo[2.2.2]octane salts [4], 1,4-difluoro-1,4-diazoniabicyclo[2.2.2]octane salts [5], 1,1'-difluoro-bipyridinium salts [6], trifluoroamine oxide [7] and 1-fluoro-2,4,6-trichloro-1,3,5-triazinium tetrafluoroborate [8].…”

Section: Introductionmentioning

confidence: 99%

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One pot synthesis of side chain fluorinated heterocyclic compounds by microwave irradiation

Khouzani

Sadeghi

Ranjbar‐Karimi

2005

JICS

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2-Or 4-Difluoronitromethyl and 2-or 4-fluoronitrobenzyl substituted pyridines, quinolines, phenantheridine, benzothiazol and benzoxazol were synthesized by reaction of the corresponding nitro compounds in the presence of 1-chloromethyl-4-fluoro-1,4-diazoiabicyclo[2,2,2]octane bis(tetrafluoroborate) (Select-Fluor) and ammonium acetate as a base under microwave irradiation. This method is very efficient and the yields were significantly improved in comparison to the previous reports.

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1-Fluoro-2,4,6-trichloro-1,3,5-triazinium tetrafluoroborate: synthesis, characterization, and ability to effect electrophilic aromatic substitution

Cited by 11 publications

References 13 publications

Fluorination of aromatic compounds with N-fluorobenzenesulfonimide under solvent-free conditions

Fluorination of aromatic compounds with N-fluorobenzenesulfonimide under solvent-free conditions

Development of N-F fluorinating agents and their fluorinations: Historical perspective

One pot synthesis of side chain fluorinated heterocyclic compounds by microwave irradiation

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