ChemInform Abstract: Iodonium Salts in Organic Synthesis

Abstract

Review: 252 refs.

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

“…Consequently, there is a rapidly growing demand for new 18 F-labelled agents to probe biological processes and targets in vivo 6 . Fluorine-18 is most readily prepared in high specific activity as no-carrier-added [ 18 aromatic/heteroaromatic substrates.…”

“…Fluorine-18 is most readily prepared in high specific activity as no-carrier-added [ 18 aromatic/heteroaromatic substrates. However, radiofluorination of non-activated arenes represents a major challenge in the field and there is an urgent need for a general and practical methodology that can introduce 18 F into molecules that cannot be labelled using a conventional S N Ar reaction.…”

“…1a, 3) [15][16][17] has been recently reviewed 18,19 . This technology has been successfully used to prepare PET radiopharmaceuticals.…”

“…This technology has been successfully used to prepare PET radiopharmaceuticals. However, 18 F-incorporation into the relatively electron-deficient (activated) arene is accompanied by production of undesired radioactive byproducts arising from the electron-rich aryl auxiliary. 17,20 Although diaryliodonium salts represent the most investigated class of hypervalent iodine(III) compounds in PET, there is scant patent literature 21 on how one might achieve the desired regiospecific radiofluorination based on the use of aryliodonium ylides (ArI ¼ CX 2 ; X¼ electron-deficient substituent) as precursors with Meldrum's acid auxiliaries.…”

Synthesis and Pharmacological Evaluation of [11C]Granisetron and [18F]Fluoropalonosetron as PET Probes for 5-HT3 Receptor Imaging

“…[47][48][49][50][51][52] To this end, we searched for methods to iodinate palonosetron (1). Direct iodination of non-activated aromatic rings is far less common than the corresponding chlorination or bromination.…”