Reaction of acetyl hypofluorite with aromatic mercury compounds: a new selective fluorination method

Visser, Gerard W.M.; HALTEREN, B. W. VON; Herscheid, J. D. M.; Briνkman, G. A.; Hoekstra, A.

doi:10.1039/c39840000655

Cited by 33 publications

(12 citation statements)

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“…With respect to the products listed in Table 1, N-phenylacetamide has been previously monofluorinated to give about a 2:1 ratio of the ortho and para regioisomers by treatment with acetyl hypofluorite 21 or 1-alkyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts (entry 1). 22 A palladium-catalyzed methylation of N-phenylacetamide selectively gave the ortho regioisomer in a 42% yield (entry 2).…”

Section: Methodsmentioning

confidence: 99%

Reductive Dehalogenation of Aryl Bromides and Chlorides and Their Use as Aryl Blocking Groups

Ramanathan¹,

Jimenez²

2009

Synthesis

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Bromo and chloro substituents serve as excellent blocking groups on aromatic rings. When a halo substituent is para to an ortho,para-directing group, the ortho positions can be easily functionalized, and the halo group can be subsequently removed by catalytic hydrogenation under neutral conditions. As expected, bromides are reduced more quickly than chlorides and the reaction requires the use of less catalyst. Bromides can be selectively reduced in the presence of nitro, chloro, cyano, keto, or carboxylic acid groups.

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Section: Methodsmentioning

confidence: 99%

Reductive Dehalogenation of Aryl Bromides and Chlorides and Their Use as Aryl Blocking Groups

Ramanathan¹,

Jimenez²

2009

Synthesis

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“…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%

“…Double fluorination through two subsequent ortho fluorinations is a problematic side reaction for the reactions shown in Fig. 69: this problem can be addressed by using the weakly coordinating anionic ortho-directing group N-perfluorotolylamide, which allows for rapid displacement of the monofluorinated product by the substrate, thus affording high selectivity for monofluorination [123][124][125][126]172]. A handful of related Pd-catalyzed electrophilic C-H fluorination reactions have since been reported, for arene substrates with a variety of coordinating directing groups [173][174][175].…”

Section: Fig 58mentioning

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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“…The aryl organometallic compounds have been prepared with a variety of metals: silicon [81-84], tin [85, 86], germanium [81], and mercury [87-89]. An L-tyrosine biological derivative, L-3,4-dihydroxyphenylalanine (L-DOPA), is a precursor to the neurotransmitters: dopamine, norepinephrine, and epinephrine.…”

Section: Strategies For Direct Electrophilic Fluorinationmentioning

confidence: 99%

Radiosyntheses using Fluorine-18: The Art and Science of Late Stage Fluorination

Cole¹,

Stewart²,

Littich³

et al. 2014

CTMC

128

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Positron (β+) emission tomography (PE) is a powerful, noninvasive tool for the in vivo, three-dimensional imaging of physiological structures and biochemical pathways. The continued growth of PET imaging relies on a corresponding increase in access to radiopharmaceuticals (biologically active molecules labeled with short-lived radionuclides such as fluorine-18). This unique need to incorporate the short-lived fluorine-18 atom (t1/2 = 109.77 min) as late in the synthetic pathway as possible has made development of methodologies that enable rapid and efficient late stage fluorination an area of research within its own right. In this review we describe strategies for radiolabeling with fluorine-18, including classical fluorine-18 radiochemistry and emerging techniques for late stage fluorination reactions, as well as labeling technologies such as microfluidics and solid-phase radiochemistry. The utility of fluorine-18 labeled radiopharmaceuticals is showcased through recent applications of PET imaging in the healthcare, personalized medicine and drug discovery settings.

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Reaction of acetyl hypofluorite with aromatic mercury compounds: a new selective fluorination method

Cited by 33 publications

References 0 publications

Reductive Dehalogenation of Aryl Bromides and Chlorides and Their Use as Aryl Blocking Groups

Reductive Dehalogenation of Aryl Bromides and Chlorides and Their Use as Aryl Blocking Groups

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

Radiosyntheses using Fluorine-18: The Art and Science of Late Stage Fluorination

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