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

Shah, Aneela; Pike, Victor W.; Widdowson, David A.

doi:10.1039/a802349b

Cited by 118 publications

(66 citation statements)

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“…As shown in Fig. 2a, the extent of such stabilization should still enable the formation of 18 F-labelled products via the addition/reductive elimination mechanism 16,24 that has been invoked for diaryliodonium salts and other I(III) species [15][16][17]20,25,26 . Initial experiments (Fig.…”

Section: Resultsmentioning

confidence: 99%

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Spirocyclic hypervalent iodine(III)-mediated radiofluorination of non-activated and hindered aromatics

et al. 2014

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Fluorine-18 (t ½ ¼ 109.7 min) is the most commonly used isotope to prepare radiopharmaceuticals for molecular imaging by positron emission tomography (PET). Nucleophilic aromatic substitution reactions of suitably activated (electron-deficient) aromatic substrates with no-carrier-added [ 18 F]fluoride ion are routinely carried out in the synthesis of radiotracers in high specific activities. Despite extensive efforts to develop a general 18 F-labelling technique for non-activated arenes there is an urgent and unmet need to achieve this goal. Here we describe an effective solution that relies on the chemistry of spirocyclic hypervalent iodine(III) complexes, which serve as precursors for rapid, one-step regioselective radiofluorination with [ 18 F]fluoride. This methodology proves to be efficient for radiolabelling a diverse range of non-activated functionalized arenes and heteroarenes, including arene substrates bearing electron-donating groups, bulky ortho functionalities, benzylic substituents and meta-substituted electron-withdrawing groups. Polyfunctional molecules and a range of previously elusive 18 F-labelled building blocks, compounds and radiopharmaceuticals are synthesized.

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Section: Resultsmentioning

confidence: 99%

“…1a, 3) [15][16][17] has been recently reviewed 18,19 . This technology has been successfully used to prepare PET radiopharmaceuticals.…”

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Spirocyclic hypervalent iodine(III)-mediated radiofluorination of non-activated and hindered aromatics

et al. 2014

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“…Symmetric and asymmetric diaryliodonium salts of target precursors, in particular, have received attention owing to their ease of preparation and compatibility with moderately electronic-rich arene systems. [7] For example, Coenen and co-workers have disclosed aryl(2-thienyl)iodonium salts as substrates of 18 F À for S N Ar which show enhanced reactivity at electron-rich homoarenes (Scheme 5 a). [8] Similarly, Pike and co-workers have shown the utility of diaryliodonium tosylates in the synthesis of mGluR5 PET radioligands (Scheme 5 b).…”

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confidence: 98%

Novel Strategies for Fluorine‐18 Radiochemistry

2011

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“…Further optimization for this and other targets is under investigation. [25,26] The Advion micro-reactor apparatus has enabled us to study the RCYs, product selectivity, kinetics and energetics of these reactions in detail ( Figure 5). [10][11][12][13][14] Conclusions: Research in our laboratory and elsewhere has clearly demonstrated that micro-reactor or microfluidics technology is well suited to PET radiotracer development and production.…”

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confidence: 99%

10th international symposium on the synthesis and applications of isotopes and isotopically labelled compounds—Professor John R. Jones memorial lectures, Monday, June 15, 2009

Hesk

2010

Labelled Comp Radiopharmac

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Abstract:The long-term collaboration with Prof. John R Jones has enabled the development or discovery of a range of one-step 3 H-and 2 H-labelling approaches. These include; (a) RhCl 3 .3H 2 O and COD.Ir.Acac catalysed ortho-exchange of aromatic acids, amides, benzylamines, anilides, sulphonamides, etc, using isotopic water as the donor in DMF or DMA solution, (b) the COD.Ir.F 6 Acac catalysed ortho-labelling of anilines, benzylamines and other N-heterocyclics using isotopic hydrogen gas in DMA at RT, (c) the a-and b-labelling of piperidines, piperazines and other secondary amines using catalytic Ru(CO) 6 Cl 2 or (C 6 H 5 ) 2 RuCl 2 with deuterium oxide in DMSO, (d) the a-labelling of pyridines and other N-heteroaromatics using rhodium and ruthenium heterogeneous catalysts with isotopic hydrogen gas in THF at RT and (e) the preparation of an efficient and clean polystyrene-based Ir(I) phosphine catalyst for the labelling of aromatic esters, aromatic ketones, sulphones, amides, anilides, etc, using isotopic hydrogen gas in dichloromethane at RT. Latterly, screening for the terminal-methylene labelling of 1-monosubstituted and 1,1-disubstituted alkenes has provided new catalytic systems for this transformation. In addition, it has provided evidence for the significance of secondary metal alkyl intermediates in the general mechanism of catalytic alkene exchange and reduction. These studies were facilitated by the application of a 3 H-NMR cryoprobe.Keywords: isotope-exchange; ortho-labelling; catalysis; alkene-exchange; hydrogenation-mechanism; deuteration; tritiation Introduction: Professor John Richards Jones was a very significant figure in the field of isotopic chemistry. His collaborations were many and varied, and his influence was very extensive. This paper describes a range of studies either carried out in conjunction with, or which received some useful input from, Prof. Jones during the 25 years of our collaboration. It describes useful labelling procedures and mechanistic investigations which have broad applications or significance for our field of science. It also gives a necessarily brief resume of the further developments which have been achieved in some of these fields since his retirement and death.For reasons of brevity other areas of our collaboration; 3 H-NMR cryoprobe development, [1a] dehalogenation studies, [1b,j] iodination methods, [1c] microwave applications, [1d] ligand receptor interactions, [1e] isotopic data processing applications [1f,g,h] and much of the work on alkene and alkyne reduction and exchange [1i,j] have been omitted, but are referenced above for those with interests in these areas. The paper therefore concentrates solely upon the following two areas.Results and Discussion: Part 1. Collaboration with AstraZeneca on tritium-labelling methods.The initial aim of the AstraZeneca (AZ)/Surrey collaboration was to produce general and practical one-step isotope exchange procedures for labelling polar xenobiotics with tritium. The project was initiated by a thorough study of the...

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

Cited by 118 publications

References 10 publications

Spirocyclic hypervalent iodine(III)-mediated radiofluorination of non-activated and hindered aromatics

Spirocyclic hypervalent iodine(III)-mediated radiofluorination of non-activated and hindered aromatics

Novel Strategies for Fluorine‐18 Radiochemistry

10th international symposium on the synthesis and applications of isotopes and isotopically labelled compounds—Professor John R. Jones memorial lectures, Monday, June 15, 2009

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