Electrophilic fluorination with N-fluoroquinuclidinium fluoride

Banks, R. E.; Boisson, R. A. Du; Tsiliopoulos, E.

doi:10.1016/s0022-1139(00)81953-3

Cited by 47 publications

(13 citation statements)

References 8 publications

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“…132, 169 ± 176 Fluoroquinuclidinium fluoride (81a) was obtained in 83% ± 89% yield by direct fluorination of quinuclidine with 10% F 2 in CFCl 3 at 778 8C. 169,171,175,176 Later, preparation of N-fluoroquinuclidinium salts with other counterions was performed by fluorination of quinuclidine in the presence of the corresponding salts (the Umemoto method). With LiOTf, N-fluoroquinuclidinium triflate (81b) was obtained in 88% yield (fluorination in MeCN at 733 8C).…”

Section: N-fluoroquinuclidinium and 4-alkyl-1-fluoro-14diazoniabicycl...mentioning

confidence: 99%

“…Thus the regio-and stereoselectivity of alkene fluorination fits well into the mechanism of formation of a fluoro carbocation as an intermediate species. 7,79,175 Alkenes in which the intermediate carbocation cannot be stabilised by substituents (e.g., oct-1-ene or cyclohexene) do not react with the fluorinating reagent 84b. As expected, polar solvents that favour the formation of a complex between the substrate and the fluorinating reagent facilitate fluorination.…”

Section: Some Examples Of Fluorination With Inorganic Tetrafluoroammo...mentioning

confidence: 99%

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N-Fluoro amines and their analogues as fluorinating reagents in organic synthesis

Fürin¹,

Fainzil'berg²

1999

Russ. Chem. Rev.

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We show that adiabatic, super-Hubble, and almost scale invariant density fluctuations are produced by cosmic strings in a contracting universe. An essential point is that isocurvature perturbations produced by topological defects such as cosmic strings on super-Hubble scales lead to a source term which seeds the growth of curvature fluctuations on these scales. Once the symmetry has been restored at high temperatures, the isocurvature seeds disappear, and the fluctuations evolve as adiabatic ones in the expanding phase. Thus, cosmic strings may be resurrected as a mechanism for generating the primordial density fluctuations observed today.

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Section: N-fluoroquinuclidinium and 4-alkyl-1-fluoro-14diazoniabicycl...mentioning

confidence: 99%

Section: Some Examples Of Fluorination With Inorganic Tetrafluoroammo...mentioning

confidence: 99%

N-Fluoro amines and their analogues as fluorinating reagents in organic synthesis

Fürin¹,

Fainzil'berg²

1999

Russ. Chem. Rev.

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“…One example of this has appeared where NFQNF (1, Figure 1) was observed to provide a 10% yield of 2-fluorothiophene from 2-lithiothiophene (Table 2, entry 5). 10 No other quinuclidine-type reagent has been utilized until quite recently. Selectfluor (F-TEDA-BF 4 ) (2, Figure 1) has the ability to effect direct electrophilic fluorinations.…”

Section: Methodsmentioning

confidence: 99%

Processing Aryllithium and Hetaryllithium Intermediates: Formation of Halogen and Chalcogen Derivatives

Slocum¹,

Shelton²,

Moran³

2005

Synthesis

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Introduction of a halogen (F, Cl, Br, I) or a chalcogen (O, S, Se, Te) via the intermediacy of an aryllithium or hetaryllithium is reviewed. Representative examples are presented to demonstrate the range of substituted aromatic compounds accessible via formation of the lithio-intermediate followed by treatment with an appropriate derivatizing agent. Where possible, the merits and the limitations of the various reagents utilized for introduction of a specific halogen or chalcogen are discussed.

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“…In 1986 as the N -F pyridinium reagents were emerging, Banks et al disclosed the quaternary ammonium N -F reagent, N -fluoroquinuclidinium fluoride ( 6-1 ) [ 43 ]. They subsequently followed with more detailed results in 1988 [ 44 ].…”

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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Electrophilic fluorination with N-fluoroquinuclidinium fluoride

Cited by 47 publications

References 8 publications

N-Fluoro amines and their analogues as fluorinating reagents in organic synthesis

N-Fluoro amines and their analogues as fluorinating reagents in organic synthesis

Processing Aryllithium and Hetaryllithium Intermediates: Formation of Halogen and Chalcogen Derivatives

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

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