ArticleThe Journal of organic chemistry2012
Regiospecific syntheses of functionalized diaryliodonium tosylates via [hydroxy(tosyloxy)iodo]arenes generated in situ from (diacetoxyiodo)arenes.
Article in The Journal of organic chemistry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- In Situ-Generated Iodine(III) Sulfonates as Versatile Oxidants for Sulfonyloxylation and Oxidative Cyclization.ACS omega · 2026Article
- Advances in α-Arylation of Carbonyl Compounds: Diaryliodonium Salts as Arylating Agents.Molecules (Basel, Switzerland) · 2025Review
- Automated synthesis ofEJNMMI radiopharmacy and chemistry · 2020Article
- Hypervalent aryliodine compounds as precursors for radiofluorination.Journal of labelled compounds & radiopharmaceuticals · 2018Review
- Cu-Mediated C-HOrganic letters · 2017Article
- [ACS chemical neuroscience · 2017Article
- Crystal Structures of Diaryliodonium Fluorides and Their Implications for Fluorination Mechanisms.Chemistry (Weinheim an der Bergstrasse, Germany) · 2017Article
- An Investigation of (Diacetoxyiodo)arenes as Precursors for Preparing No-Carrier-Added [(18)F]Fluoroarenes from Cyclotron-Produced [(18)F]Fluoride Ion.The Journal of organic chemistry · 2016Article
- Synthesis and evaluation in monkey of [(18)F]4-fluoro-N-methyl-N-(4-(6-(methylamino)pyrimidin-4-yl)thiazol-2-yl)benzamide ([(18)F]FIMX): a promising radioligand for PET imaging of brain metabotropic glutamate receptor 1 (mGluR1).Journal of medicinal chemistry · 2013Article
- Single-step syntheses of no-carrier-added functionalized [18F]fluoroarenes as labeling synthons from diaryliodonium salts.Organic & biomolecular chemistry · 2013Article
- 4-[18F]Fluoro-m-hydroxyphenethylguanidine: a radiopharmaceutical for quantifying regional cardiac sympathetic nerve density with positron emission tomography.Journal of medicinal chemistry · 2013Article
- Single-step Radiosyntheses of 'European journal of organic chemistry · 2012Article
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2 authors.
Funding
Abstract
Ready access to (18)F-labeled aryl synthons is required for preparing novel radiotracers for molecular imaging with positron emission tomography. Diaryliodonium salts react with cyclotron-produced no-carrier-added [(18)F]fluoride ion to produce [(18)F]aryl fluorides. We aimed to prepare functionalized diaryliodonium salts to serve as potential precursors for producing useful (18)F-labeled aryl synthons, such as (18)F-labeled halomethylbenzenes, benzaldehydes, and benzoic acid esters. Such salts were designed to have one functionalized aryl ring, one relatively electron-rich ring, such as 4-methoxyphenyl or 2-thienyl, and a nonfluorine containing weakly nucleophilic anion. Generation of a [hydroxy(tosyloxy)iodo]arene from a functionalized (diacetoxyiodo)arene in situ followed by treatment with an electron-rich arene, such as anisole or thiophene, or with a functionalized arylstannane gave expedient regiospecific access to a wide range of functionally diverse diaryliodonium tosylates in moderate to high yields (44-98%). The described methodology broadens the scope for producing new functionalized diaryliodonium salts for diverse applications.
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