Radioiodination techniques for small organic molecules

Seevers, Robert H.; Counsell, Raymond E.

doi:10.1021/cr00052a002

Cited by 278 publications

(150 citation statements)

References 45 publications

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“…HPLC analysis (radio channel) of the 125 I labeling of lidocaine analogue 11. mation, Scheme S1, for details). [22] Another popular method for iodination of aromatics through ipso substitution of an activator group is by use of arylstannanes, [5,23] which are typically converted into the corresponding aryl iodide by treatment with NaI and chloramine T (or another oxidant such as peracetic acid) in an acidic aqueous environment. Hence, the use of TMS-aryls and Tl(OCOCF 3 ) 3 is an attractive alternative to arylstannanes, especially for molecules with low water solubility and for substrates that are sensitive to highly acidic environments (such as neat TFA) or oxidizing reagents.…”

Section: Resultsmentioning

confidence: 99%

“…[2] Owing to emission of gamma radiation, iodinated radiopharmaceuticals are also used in scintigraphic imaging for disease diagnostics, [3] for example, in the localization of tumors by use of meta-iodobenzylguanidine (MIBG) labeled with 123 I. [4] The iodination of aromatics can be achieved by different methods, [5] and the choice of labeling method depends very much on the substrate. Many of the most widely used labeling techniques involve the use of oxidizing agents such as chloramine T, [6] iodogen, [7] and lactoperoxidase; [8] however, these methods suffer from low selectivity and are restricted to activated aromatics.…”

Section: Introductionmentioning

confidence: 99%

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A Mild Method for Regioselective Labeling of Aromatics with Radioactive Iodine

et al. 2013

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A Mild Method for Regioselective Labeling of Aromatics with Radioactive Iodine

et al. 2013

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“…1b). Moreover, aryl iodides are useful in their own right and have already found wide application in the medical research field, for example, in hypothyroidism treatment, single-photon-emission computed tomography and preclinical X-ray imaging [4][5][6][7] . The existence of different radioactive iodine isotopes ( 131 I, 125 I, 123 I) also makes it possible to label the same target agent with different isotopes, which provides additional flexibility in pharmacokinetic studies.…”

Section: Introductionmentioning

confidence: 99%

Photo-induced iodination of aryl halides under very mild conditions

Liu

et al. 2016

Nat Protoc

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Aryl iodides are important precursors in synthetic chemistry that form carbon–carbon and carbon–heteroatom bonds. Most methods use transition-metal catalysts, which need to be scrupulously removed before the compounds can be used in the pharmaceutical and electronics industries, where only parts-per-million levels of transition metals are allowed. The aromatic Finkelstein iodination reaction is a powerful method of preparing valuable aryl iodides from cheap but less reactive aryl bromides and chlorides. This protocol describes a transition metal–free method for a photo-induced aromatic Finkelstein iodination reaction that is performed at room temperature (20 °C). With common aromatic bromides and sodium iodide (NaI) as the starting materials, as well as a catalytic amount of I2 as an additive, the corresponding aromatic iodides can be synthesized in yields ranging from 56 to 93% under UV light irradiation in the absence of any metal catalysts. Various functional groups such as nitrile, ester and amino can be tolerated, which will facilitate the further functionalization of the aromatic iodides. The procedure normally requires 38–40 h to complete

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“…12,13 Continuing interest of organic chemists in iodination reactions are due to the versatility of iodinated compounds as building blocks in a variety of synthetic transformations in medicinal chemistry, as well as in the biomedical sciences as imaging agents in non-invasive medical diagnostic techniques due to the possible release of the long-lived radioactive 129 I isotope. [14][15][16][17][18] In the 1950's the hormone thyroxine and its analogues were prepared as radioiodinated photoprobes. [19][20][21][22][23] A broad range of procedures are described in the literature for the iodination of phenols, involving the use of NIS, ICl, I 2 and iodides salts in the presence of an oxidant, in acid or basic conditions.…”

Section: Introductionmentioning

confidence: 99%

Iodination of phenols in water using easy to handle amine-iodine complexes

Frota¹,

Canavez²,

Gomes³

et al. 2009

J. Braz. Chem. Soc.

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A reação entre o iodo e a N-metil-piperazina ou a tiomorfolina em água, na presença de KI, levou a formação de complexos amina-iodo estáveis e de fácil manipulação, tal qual o complexo morfolina-iodo, previamente descrito na literatura. Entretanto, o complexo formado entre o iodo e a N,N-tetrametiletilenodiamina mostrou-se pouco estável, enquanto que nenhum complexo foi isolado quando a piperidina foi usada como base. Estes resultados mostram que a presença do segundo heteroátomo na estrutura das aminas é fundamental para a formação e estabilidade desses complexos. Neste trabalho descrevemos, pela primeira vez, o emprego dos complexos morfolina-iodo, N-metil-piperazina-iodo e tiomorfolina-iodo como agentes de iodação de vários fenóis substituídos, conduzindo a uma série de produtos iodados em rendimentos variando de bons a excelentes.The reaction between iodo and N-methyl-piperazine or thiomorpholine in water, in the presence of KI, led to the formation of stable and easy to handle amine-iodine complexes, as the complex morpholine-iodo previously reported in the literature. However, the complex obtained using N,Ntetrametylethylenediamine proved less stable, while no complex was formed when piperidine was used as base. These results show that the presence of a second heteroatom in the structure of amines is of fundamental importance for the formation and stability of these complexes. In this work we describe, for the first time, the use of complexes morpholine-iodo, N-methyl-piperazine-iodo and thiomorpholine-iodo as iodinating reagents of several substituted phenols, leading to iodinated products in good to excellent yields.

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Radioiodination techniques for small organic molecules

Cited by 278 publications

References 45 publications

A Mild Method for Regioselective Labeling of Aromatics with Radioactive Iodine

A Mild Method for Regioselective Labeling of Aromatics with Radioactive Iodine

Photo-induced iodination of aryl halides under very mild conditions

Iodination of phenols in water using easy to handle amine-iodine complexes

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