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

Benjamin H. Rotstein, Nickeisha A. Stephenson, Neil Vasdev () and Steven H. Liang ()
Additional contact information
Benjamin H. Rotstein: Center for Advanced Medical Imaging Sciences, Harvard Medical School
Nickeisha A. Stephenson: Center for Advanced Medical Imaging Sciences, Harvard Medical School
Neil Vasdev: Center for Advanced Medical Imaging Sciences, Harvard Medical School
Steven H. Liang: Center for Advanced Medical Imaging Sciences, Harvard Medical School

Nature Communications, 2014, vol. 5, issue 1, 1-7

Abstract: Abstract Fluorine-18 (t½=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 [18F]fluoride ion are routinely carried out in the synthesis of radiotracers in high specific activities. Despite extensive efforts to develop a general 18F-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 [18F]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 18F-labelled building blocks, compounds and radiopharmaceuticals are synthesized.

Date: 2014
References: Add references at CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/ncomms5365 Abstract (text/html)

Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.

Export reference: BibTeX RIS (EndNote, ProCite, RefMan) HTML/Text

Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:5:y:2014:i:1:d:10.1038_ncomms5365

Ordering information: This journal article can be ordered from
https://www.nature.com/ncomms/

DOI: 10.1038/ncomms5365

Access Statistics for this article

Nature Communications is currently edited by Nathalie Le Bot, Enda Bergin and Fiona Gillespie

More articles in Nature Communications from Nature
Bibliographic data for series maintained by Sonal Shukla () and Springer Nature Abstracting and Indexing ().