103185-00-8

Upstream product

• 6999-03-7 1-bromo-4-(trimethylsilyl)benzene 
• 65826-67-7 bis(4-bromophenyl)iodonium bromide 
• 139139-81-4 bis(4-bromophenyl)iodonium triflate 
• 589-87-7 1,4-bromoiodobenzene 
• 1774-37-4 bis(4-bromophenyl)sulfoxide 
• 108-86-1 bromobenzene 
• 255056-44-1 4-bromophenyldiphenylsulfonium triflate 
• 586-78-7 para-nitrophenyl bromide 
• 106-37-6 1.4-dibromobenzene 
• 205930-68-3 2-(⁽¹⁸⁾F)fluoro-5-bromobenzaldehyde 
• 144930-53-0 (4-bromophenyl)(phenyl)iodonium triflate 
• 937-11-1 (4-bromophenyl)trimethylstannane 
• 33733-44-7 (4-bromophenyl)trimethylgermane 

Downstream Products

• 146354-01-0 [18F]2-[3-(4-(4-fluorophenyl)-1-piperazinyl)propyl]naphtho[1,8-cd]isothiazole-1,1-dioxide 
• 3857-04-3 [18F]fluorobenzene 

Relevant academic research and scientific papers

[18F]Fluorophenyl organometallics as intermediates of no-carrier-added 18F-fluoroarylation reactions

Based on the recent availability of no-carrier-added (n.c.a.) 1-bromo-4-[18F]fluorobenzene with high radiochemical yield, the 4-[18F]fluorophenyl compounds of lithium, sodium and magnesium can now also effectively be prepared. Thus,

Nucleophilic 18F-fluorination of heteroaromatic iodonium salts with no-carrier-added [18F]fluoride

Diaryliodonium salts containing the 2-thienyl group as an example of an electron-rich heteroaromatic moiety proved to be very potent precursors for the nucleophilic, regioselective no-carrier-added (nca) radiofluorination of various arenes. It even allowe

ELECTROPHILIC RADIOFLUORATION OF ARYLTRIMETHYLSILANES AS A GENERAL ROUTE TO 18F-LABELED ARYL FLUORIDES

The reaction of a variety of aryltrimethylsilanes with elemental fluorine and acetyl hypofluorite have been studied with the aim of developing a general method for labeling aromatic compounds with fluorine-18.Extensive 18F incorporation into the aromatic ring of the selected aryltrimethylsilanes was invariably observed, leading to the ipso(18F-for Si) electrophilic substitution products together with variable yields of other (18F-for-H) electrophilic substitution products.The relative extent of the 18F substitution processes subst.> is found to depend largely upon the substituent group on the aromatic ring of the substrate, the leaving moiety, and the radiofluoration procedure used.The utility of aryltrimethylsilyl derivates as precursors for the rapid synthesis of high specific activity of 18F-labeled radiopharmaceuticals is discussed.

Comparison of pathways to the versatile synthon of no-carrier-added 1-bromo-4-[18F]fluorobenzene

The availability of no-carrier-added (n.c.a.) 1-bromo-4-[ 18F]fluorobenzene with high radiochemical yields is important for 18F-arylation reactions using metallo-organic 4-[18F] fluorophenyl compounds (e.g. of lithium or m

REGIOSPECIFIC AROMATIC FLUORODEMETALLATION OF GROUP IVb METALLOARENES USING ELEMENTAL FLUORINE OR ACETYL HYPOFLUORITE

The reactions of fluorine and acetyl hypofluorite with trimethylaryltin,- germanium, and- silicon compounds were studied using fluorine-18 (T1/2 = 110 min) as a radiochemical tracer.The fluoro-demetallation of phenyl derivatives by sub-stoichio

Catalyst-Free Aromatic Radiofluorination via Oxidized Iodoarene Precursors

Oxidized iodoarenes (OIAs), prepared via mCPBA-mediated oxidation, have been demonstrated as versatile precursors for the synthesis of [18F]fluoroarenes in the absence of catalysts. OIAs have been identified as intermediates in single-pot syntheses of iodonium salts and ylides but have never been recognized as radiofluorination precursors. Here, the isolated OIAs were used without any catalysts to produce functionalized [18F]fluoroarenes, regardless of the electronic nature of the arenes. This method was also applied to the production of radiolabeling synthons for use as aromatic 18F-labeled building blocks.

No-carrier-added [18F]fluoroarenes from the radiofluorination of diaryl sulfoxides

No-carrier-added [18F]fluoroarenes were synthesized through the radiofluorination of diaryl sulfoxides with [18F]fluoride ion. Diaryl sulfoxides bearing a para electron-withdrawing substituent readily gave the corresponding 4-[18F]fluoroarenes in high RCYs. This process broadens the scope for preparing novel 18F-labeling synthons and PET radiotracers.

18F-radiolabeling of aromatic compounds using triarylsulfonium salts

A new method for the 18F-radiolabeling of aromatic compounds based on the aromatic nucleophilic substitution (SNAr) reaction using triarylsulfonium salts has been developed. Experiments and DFT calculations indicated that sulfonium i

NO-CARRIER-ADDED NUCLEOPHILIC [F-18] FLUORINATION OF AROMATIC COMPOUNDS

Phenyliodonium ylide derivatives substituted with electron donating as well as electron withdrawing groups on the aromatic ring are shown for use as precursors in aromatic nucleophilic substitution reactions. The iodonium ylide group is substituted by nucleophiles such as halide ions to provide the corresponding haloaryl derivatives. No- carrier-added [F-18]fluoride ion exclusively substitutes the iodonium ylide moiety in these derivatives and provides high specific activity F- 18 labeled fluoro derivatives. Protected L-dopa-6-iodonium ylide derivative have been synthesized as a precursors for the preparation of no-carrier-added 6-[F- 18]fluoro-L-dopa. The iodonium ylide group in this L-dopa.derivative is nucleophilically substituted by no-carrier-added [F-18]fluoride ion to provide a [F-18]fluoro intermediates which upon acid hydrolysis yielded 6-[F- 18]fluoro-L-dopa.

The synthesis of [18F]fluoroarenes from the reaction of cyclotron-produced [18F]fluoride ion with diaryliodonium salts

Diaryliodonium salts have been shown to react with fluoride ion at 80°C in acetonitrile to generate aryl fluorides. The regioselectivity is controlled electronically and by the bulk of the ortho-substituents on the rings, with the latter the dominant factor such that electron-rich rings can be fluorinated. ortho-Substituted aryl fluorides can be selectively produced from unsymmetrical diaryliodonium salts. The process has been used to synthesise [18F] labelled aromatics by the use of cyclotron generated [18F]fluoride ion.