Evaluation of aromatic radiobromination by nucleophilic substitution using diaryliodonium salt precursors

Zhou, Dong; Kim, Sung Hoon; Chu, Wenhua; Voller, Thomas; Katzenellenbogen, John A.

doi:10.1002/jlcr.3519

Evaluation of aromatic radiobromination by nucleophilic substitution using diaryliodonium salt precursors

Journal Article · Wed May 17 00:00:00 EDT 2017 · Journal of Labelled Compounds and Radiopharmaceuticals

DOI:https://doi.org/10.1002/jlcr.3519· OSTI ID:1533183

^[1]; Kim, Sung Hoon ^[2]; Chu, Wenhua ^[3]; Voller, Thomas ^[3]; Katzenellenbogen, John A. ^[2]

Washington Univ., St. Louis, MO (United States); DOE/OSTI
Univ. of Illinois at Urbana-Champaign, IL (United States)
Washington Univ., St. Louis, MO (United States)

Radiobromine-labeled compounds can be used for positron emission tomography (PET) imaging (ie, ⁷⁶Br) and for radiation therapy (ie, ⁷⁷Br). However, the commonly used electrophilic substitution reaction using no-carrier-added radiobromide does not always afford the desired product due to the high reactivity of the brominating intermediate. A nucleophilic substitution by bromide, such as radiobromination of iodonium precursors, provides an alternative route for the synthesis of bromo-radiopharmaceuticals. The applicability of aromatic radiobromination by nucleophilic substitution using diaryliodonium salt precursors was evaluated using iodonium model compounds and [⁷⁶Br]/[⁷⁷Br]bromide. Radiobromination was observed under all conditions tested, in up to quantitative yields. A QMA cartridge treatment method and a base-free method have been developed, and no extra base is needed for either methods. The base-free conditions are mild and afford much cleaner reactions. Up to 20% water is tolerated in the reactions without reducing the radiochemical yields. No-carrier-added and carrier-added reactions afforded similar results. 4-Bromobenzaldehyde and 4-bromobenzoate have been radiosynthesized reliably and in good yields. Finally, these results indicate that this method is robust and efficient and thus will provide a route for radiobromination of electron-deficient arenes and an alternative route for the synthesis of bromo-radiopharmaceuticals for biological evaluations.

View Accepted Manuscript (DOE)

Research Organization:: Washington Univ., St. Louis, MO (United States)

Sponsoring Organization:: National Institutes of Health (NIH); USDOE; USDOE Office of Science (SC)

Grant/Contract Number:: SC0008432

OSTI ID:: 1533183

Alternate ID(s):: OSTI ID: 1401796

Journal Information:: Journal of Labelled Compounds and Radiopharmaceuticals, Journal Name: Journal of Labelled Compounds and Radiopharmaceuticals Journal Issue: 9 Vol. 60; ISSN 0362-4803

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

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Cited By (2)

Base/Cryptand/Metal-Free Automated Nucleophilic Radiofluorination of [ ¹⁸ F]FDOPA from Iodonium Salts: Importance of Hydrogen Carbonate Counterion : Base/Cryptand/Metal-Free Automated Nucleophilic Radiofluorination of [ Maisonial-Besset, Aurélie; Serre, Audrey; Ouadi, Ali European Journal of Organic Chemistry, Vol. 2018, Issue 48 https://doi.org/10.1002/ejoc.201801608	journal	December 2018
The first radiosynthesis of 2-amino-5-[ ¹⁸ F]fluoropyridines via a “minimalist” radiofluorination/palladium-catalyzed amination sequence from anisyl(2-bromopyridinyl)iodonium triflate Pauton, Mathilde; Gillet, Raphaël; Aubert, Catherine Organic & Biomolecular Chemistry, Vol. 17, Issue 26 https://doi.org/10.1039/c9ob01187k	journal	January 2019

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Evaluation of aromatic radiobromination by nucleophilic substitution using diaryliodonium salt precursors

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