Aryl fluoride syntheses involving reaction of aryllead triacetates with boron trifluoride-diethyl ether complex

Meio, G. De; Morgan, J.; Pinhey, John T.

doi:10.1016/s0040-4020(01)88032-7

Cited by 27 publications

(24 citation statements)

References 29 publications

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“…The remaining reaction mixture was poured onto ice and extracted with dichloromethane (3 × 150 mL). The combined organic extracts were dried (MgSO 4 ) and evaporated to give a brown oil that was purified by vacuum distillation to give 1-fluoro-2,6-dimethylbenzene: NMR data were in agreement with published data 17a…”

Section: Methodssupporting

confidence: 89%

Liquid-Phase Decarboxylation of Aromatic Haloformates: A New Access to Chloro- and Fluoroaromatics

1998

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The treatment of phenyl chloroformates 1 with a Lewis acid in the liquid phase resulted in decarboxylation to the corresponding chloroaromatics 2. Fluoroaromatic compounds were synthesized from phenylchloroformates 1 through a sequential fluorination/decarboxylation in the liquid phase by treatment with excess anhydrous hydrogen fluoride under mild conditions. In all cases, yields were increased by performing the reaction in 1,2,4-trichlorobenzene, which is inert to Friedel-Crafts reactions.

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Section: Methodssupporting

confidence: 89%

Liquid-Phase Decarboxylation of Aromatic Haloformates: A New Access to Chloro- and Fluoroaromatics

1998

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“…The Yu group subsequently reported a C-H fluorination of N-benzyltriflamide derivatives (Fig. 69, bottom) [120][121][122]171]. These Pd-catalyzed fluorination reactions were the first examples of transition-metal-catalyzed aromatic fluorination.…”

Section: Fig 58mentioning

confidence: 99%

“…While direct electrophilic fluorination of a variety of aryl nucleophiles has been reported-including aryl boron [117,118], germanium [119], lead [120][121][122], mercury [123][124][125][126], silicon [127][128][129][130][131][132], and tin [119,120,123,[133][134][135][136][137][138] reagents-the substrate scope is typically limited and unselective fluorination is often observed. The use of a transition metal catalyst or mediator can enable more selective arene fluorination, using milder conditions and less reactive electrophilic fluorinating reagents such as Selectfluor (F-TEDA-BF 4 ) [83,139], N-fluorobenzenesulfonimide (NFBS) [12,[140][141][142][143][144], and N-fluoropyridinium salts [3,[84][85][86][87][145][146][147][148][149][150].…”

Section: Electrophilic Arene Fluorinationmentioning

confidence: 99%

Transition Metal-Mediated and Metal-Catalyzed Carbon–Fluorine Bond Formation

Campbell

Hoover

Ritter

2014

Topics in Organometallic Chemistry

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The development of new C-F bond forming reactions from organotransition metal complexes has played a key role in advancing the field of fluorination chemistry and has allowed for improved access to fluorinated organic molecules of interest in medicine, materials, and agrochemicals. In this review, we describe the development of transition metal-mediated and metal-catalyzed fluorination methods over the past decade. Special attention is paid to the variety of organometallic mechanisms by which C-F bond formation can occur and the strengths and limitations of different approaches.

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“…As a versatile, cheap, and easily handled Lewis acid, BF 3 ·Et 2 O could also act as a fluorine source in various fluorination reactions. 17 Among them, aminofluorinations could result in fluorinated N -compounds, including useful N -heterocycles ( Scheme 1 b). 18 In view of operational and environmental advantages associated with hypervalent iodine reagent applied in fluorination reactions, 15 , 19 we recently reported hypervalent iodine-catalyzed fluorinations using BF 3 ·Et 2 O as s fluorine source.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Synthesis of 5-Fluoro-2-oxazolines: Using BF₃·Et₂O as the Fluorine Source and Activating Reagent

et al. 2022

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Hypervalent iodine catalyst-catalyzed nucleophilic fluorination of unsaturated amides using BF 3 ·Et 2 O as the fluorine source and activating reagent was reported. Various 5-fluoro-2-oxazoline derivatives were synthesized in good to excellent yields (up to 95% isolated yield) within 10 min. The process was efficient and metal-free under mild conditions. A mechanism involving a fluorination/1,2-aryl migration/cyclization cascade was proposed on the basis of previous work and experimental results.

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Aryl fluoride syntheses involving reaction of aryllead triacetates with boron trifluoride-diethyl ether complex

Cited by 27 publications

References 29 publications

Liquid-Phase Decarboxylation of Aromatic Haloformates: A New Access to Chloro- and Fluoroaromatics

Liquid-Phase Decarboxylation of Aromatic Haloformates: A New Access to Chloro- and Fluoroaromatics

Transition Metal-Mediated and Metal-Catalyzed Carbon–Fluorine Bond Formation

Catalytic Synthesis of 5-Fluoro-2-oxazolines: Using BF₃·Et₂O as the Fluorine Source and Activating Reagent

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Aryl fluoride syntheses involving reaction of aryllead triacetates with boron trifluoride-diethyl ether complex

Cited by 27 publications

References 29 publications

Liquid-Phase Decarboxylation of Aromatic Haloformates: A New Access to Chloro- and Fluoroaromatics

Liquid-Phase Decarboxylation of Aromatic Haloformates: A New Access to Chloro- and Fluoroaromatics

Transition Metal-Mediated and Metal-Catalyzed Carbon–Fluorine Bond Formation

Catalytic Synthesis of 5-Fluoro-2-oxazolines: Using BF3·Et2O as the Fluorine Source and Activating Reagent

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Catalytic Synthesis of 5-Fluoro-2-oxazolines: Using BF₃·Et₂O as the Fluorine Source and Activating Reagent