ArticleChemistry (Weinheim an der Bergstrasse, Germany)2016
Unexpected Behavior of the Heaviest Halogen Astatine in the Nucleophilic Substitution of Aryliodonium Salts.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed, 51 citations in OpenAlex.
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- Iodoarene Activation: Take a Leap Forward toward Green and Sustainable Transformations.Chemical reviews · 2025Review
- Astatine-211 radiolabelling chemistry: from basics to advanced biological applications.EJNMMI radiopharmacy and chemistry · 2024Review
- The Different Strategies for the Radiolabeling of [Pharmaceutics · 2024Review
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- Synthesis of Radioiodinated Compounds. Classical Approaches and Achievements of Recent Years.International journal of molecular sciences · 2022Review
- Overview of the Most Promising Radionuclides for Targeted Alpha Therapy: The "Hopeful Eight".Pharmaceutics · 2021Review
- Investigation on the reactivity of nucleophilic radiohalogens with arylboronic acids in water: access to an efficient single-step method for the radioiodination and astatination of antibodies.Chemical science · 2020Article
- Rapid Cu-Catalyzed [Organic letters · 2018Article
- Experimental and computational evidence of halogen bonds involving astatine.Nature chemistry · 2018Article
- Pd(0)-MediatedThe Journal of organic chemistry · 2017Article
- Bifunctional aryliodonium salts for highly efficient radioiodination and astatination of antibodies.Bioorganic & medicinal chemistry · 2017Article
- Evaluation of aromatic radiobromination by nucleophilic substitution using diaryliodonium salt precursors.Journal of labelled compounds & radiopharmaceuticals · 2017Article
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Authors and funding
5 authors at 2 institutions in 2 countries.
Funding
Abstract
Aryliodonium salts have become precursors of choice for the synthesis of (18) F-labeled tracers for nuclear imaging. However, little is known on the reactivity of these compounds with heavy halides, that is, radioiodide and astatide, at the radiotracer scale. In the first comparative study of radiohalogenation of aryliodonium salts with (125) I(-) and (211) At(-) , initial experiments on a model compound highlight the higher reactivity of astatide compared to iodide, which could not be anticipated from the trends previously observed within the halogen series. Kinetic studies indicate a significant difference in activation energy (Ea =23.5 and 17.1 kcal mol(-1) with (125) I(-) and (211) At(-) , respectively). Quantum chemical calculations suggest that astatination occurs via the monomeric form of an iodonium complex whereas iodination occurs via a heterodimeric iodonium intermediate. The good to excellent regioselectivity of halogenation and high yields achieved with diversely substituted aryliodonium salts indicate that this class of compounds is a promising alternative to the stannane chemistry currently used for heavy radiohalogen labeling of tracers in nuclear medicine.
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