Base-Mediated Radio-Iodination of Arenes by Using Organosilane and Organogermane as Radiolabelling Precursors

Hugo Bloux; Amit Dahiya; Alexandra Hébert; Frédéric Fabis; Franziska Schoenebeck; Thomas Cailly

doi:10.1002/chem.202203366

Base-Mediated Radio-Iodination of Arenes by Using Organosilane and Organogermane as Radiolabelling Precursors

Chemistry. 2023 Apr 3;29(19):e202203366. doi: 10.1002/chem.202203366. Epub 2023 Mar 1.

Authors

Hugo Bloux¹, Amit Dahiya², Alexandra Hébert¹, Frédéric Fabis¹, Franziska Schoenebeck², Thomas Cailly^{1

3

4

5}

Affiliations

¹ Centre d'Etudes et de Recherche sur le Médicament de Normandie (CERMN), Normandie Univ, UNICAEN, 14000, Caen, France.
² Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.
³ IMOGERE, Normandie Univ, UNICAEN, 14000, Caen, France.
⁴ Department of Nuclear Medicine, CHU Côte de Nacre, 14000, Caen, France.
⁵ Institut Blood and Brain @Caen-Normandie (BB@C), Boulevard Henri Becquerel, 14074, Caen, France.

PMID: 36607172
DOI: 10.1002/chem.202203366

Abstract

The radio-iodination of arenes is investigated from organosilane and organogermane precursors using ipso-electrophilic halogenation (IEH). Discovery of a mild base mediated process allows radio-iodination in HFIP (1,1,1,3,3,3-hexafluoro-2-propanol) of either aryl silane or germane, with germanes being more reactive. Clinical potential of arylgermanes as radio-iodination precursors is demonstrated through the labelling of [¹²⁵ I]IMTO (iodometomidate) and [¹²⁵ I]MIBG (meta-iodobenzylguanidine) thus offering an alternative to radio-iododestannylation processes using non-toxic precursors.

Keywords: electrophilic substitution; germanes; iodine; radiochemistry; silanes.

Abstract

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