Nickel‐Mediated Radioiodination of Aryl and Heteroaryl Bromides: Rapid Synthesis of Tracers for SPECT Imaging

Cant, Alastair A.; Champion, Sue; Bhalla, Rajiv; Pimlott, Sally L.; Sutherland, Andrew

doi:10.1002/ange.201302800

Cited by 7 publications

(2 citation statements)

References 26 publications

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“…7,8 Several radiochemical methods for the labeling of biomolecules or small molecules with iodine radioisotopes have been developed. [9][10][11][12][13] Among them, electrophilic aromatic substitution reaction has widely been applied to the radiolabeling of tyrosine-containing peptide or proteins. In many cases, this method offered a simple synthetic procedure and high labeling efficiency.…”

Section: Introductionmentioning

confidence: 99%

Efficient method for iodine radioisotope labeling of cyclooctyne-containing molecules using strain-promoted copper-free click reaction

Jeon

Kang

Shim

et al. 2015

Bioorganic & Medicinal Chemistry

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Section: Introductionmentioning

confidence: 99%

Efficient method for iodine radioisotope labeling of cyclooctyne-containing molecules using strain-promoted copper-free click reaction

Jeon

Kang

Shim

et al. 2015

Bioorganic & Medicinal Chemistry

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“…Alternative approaches have been developed to improve these issues. For example, in the nickel‐mediated direct radioiodination of aryl and heteroaryl bromides, 6 this halogen‐exchange reaction carried out at high temperatures (e.g., 180°C) employs Ni(cod) 2 , an air‐sensitive metal complex requiring storage at 0°C and inert atmosphere techniques for handling. Therefore, Ni‐based precursors are not trivial to prepare by non‐chemist professionals performing (pre)clinical studies.…”

Section: Introductionmentioning

confidence: 99%

Copper‐mediated radioiodination reaction through aryl boronic acid or ester precursor and its application to direct radiolabeling of a cyclic peptide

Kondo

Kimura

Fukumoto

et al. 2021

Labelled Comp Radiopharmac

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A copper‐mediated radioiodination using aryl boronic precursors is attracting attention as a solution to oxidative iododestannylation and nickel‐mediated radioiodination drawbacks. The copper‐mediated radiolabeling method allows radioiodination at room temperature with stable aryl boronic precursors without preparing complex starting materials or reagents and can be performed in a reaction vessel exposed to air. This method has good potential in radiochemistry; however, studies on the scope of copper‐mediated radioiodination through boronic precursors are insufficient. In particular, few reports have demonstrated the effect of protecting groups on radiolabeling efficiency. Therefore, the effect of the protecting group of aryl boronic acids on the copper‐mediated radioiodination was investigated. In addition, this method, which does not require heating, is expected to be useful for direct radiolabeling of peptides. Thus, we attempted direct radioiodination of c(RGDyk) as an example. The resulting radioiodination method was well tolerated in various substrates and was unaffected by the pinacol ester‐type protecting group. Also, c(RGDyk) was labeled with 125I via copper‐mediated radioiodination using an aryl boronic acid precursor. The reaction time and yield were improved, compared with the indirect method. Furthermore, the large difference in polarity between the boronic acid precursor and the radiolabeled compound facilitated purification.

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Orthogonal Stability and Reactivity of Aryl Germanes Enables Rapid and Selective (Multi)Halogenations

2020

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While halogenation is of key importance in synthesis and radioimaging,t he currently available repertoire is largely designed to introduce as ingle halogen per molecule.T his report makes the selective introduction of several different halogens accessible.S howcased here is the privileged stability of nontoxicaryl germanes under harsh fluorination conditions (that allows elective fluorination in their presence), while displaying superior reactivity and functional-group tolerance in electrophilic iodinations and brominations,o utcompeting silanes or boronic esters under rapid and additive-free conditions.M echanistic experiments and computational studies suggest ac oncerted electrophilic aromatic substitution as the underlying mechanism.

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Nickel‐Mediated Radioiodination of Aryl and Heteroaryl Bromides: Rapid Synthesis of Tracers for SPECT Imaging

Cited by 7 publications

References 26 publications

Efficient method for iodine radioisotope labeling of cyclooctyne-containing molecules using strain-promoted copper-free click reaction

Efficient method for iodine radioisotope labeling of cyclooctyne-containing molecules using strain-promoted copper-free click reaction

Copper‐mediated radioiodination reaction through aryl boronic acid or ester precursor and its application to direct radiolabeling of a cyclic peptide

Orthogonal Stability and Reactivity of Aryl Germanes Enables Rapid and Selective (Multi)Halogenations

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