Carbon‐11 carboxylation of terminal alkynes with [<sup>11</sup>C]CO<sub>2</sub>

Goudou, Francesca; Gee, Antony D.; Bongarzone, Salvatore

doi:10.1002/jlcr.3907

Cited by 4 publications

(2 citation statements)

References 34 publications

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“…After optimization of the original reaction conditions (CuI instead of CuTC, NMP instead of DMF and addition of TBAT as fluoride ion source), two tetrazines were successfully 11 C-carboxylated with RCYs of 10–15% and “clicked” to the TCO-PeptoBrushes. It is noteworthy that Goudou et al reported the copper-catalyzed radiosynthesis of [ 11 C]carboxylic acids by reaction of [ 11 C]CO 2 with terminal alkynes in presence of DBU (see Scheme 2 B) [ 28 ]. A small library of [ 11 C]propiolic acids was obtained with RCYs between 7 and 28%.…”

Section: Carbon-11 Methodologiesmentioning

confidence: 99%

Recent Developments in Carbon-11 Chemistry and Applications for First-In-Human PET Studies

et al. 2023

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Positron emission tomography (PET) is a molecular imaging technique that makes use of radiolabelled molecules for in vivo evaluation. Carbon-11 is a frequently used radionuclide for the labelling of small molecule PET tracers and can be incorporated into organic molecules without changing their physicochemical properties. While the short half-life of carbon-11 (11C; t½ = 20.4 min) offers other advantages for imaging including multiple PET scans in the same subject on the same day, its use is limited to facilities that have an on-site cyclotron, and the radiochemical transformations are consequently more restrictive. Many researchers have embraced this challenge by discovering novel carbon-11 radiolabelling methodologies to broaden the synthetic versatility of this radionuclide. This review presents new carbon-11 building blocks and radiochemical transformations as well as PET tracers that have advanced to first-in-human studies over the past five years.

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Section: Carbon-11 Methodologiesmentioning

confidence: 99%

Recent Developments in Carbon-11 Chemistry and Applications for First-In-Human PET Studies

et al. 2023

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“…Using simple CuCl as a catalyst, the propiolic acid products were obtained in good to excellent yields. Very recently, Bongarzone and co‐workers developed a copper‐catalyzed radiosynthesis of carbon‐11 radiolabelled carboxylic acids via the carboxylation of terminal alkynes with cyclotron‐produced carbon‐11 carbon dioxide ([ 11 C]CO 2 ) [50] . Several 11 C‐labelled propiolic acid products were delivered with a radiochemical yield (RCY) ranging from 7 % to 28 %, highlighting the potential application of this method to PET imaging in metabolic diseases by radiolabeling some specific molecules.…”

Section: Copper‐catalyzed Carboxylation Of C−c Triple Bondsmentioning

confidence: 99%

Recent Advances in Copper‐Catalyzed Carboxylation Reactions with CO₂

Song

Chen

2022

Asian J Org Chem

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As an ideal one-carbon synthon, CO 2 has been successfully utilized in diverse carboxylation reactions to construct a series of value-added products. Among various transition-metal catalysts, the inexpensive copper complexes exhibit unique catalytic activity in carboxylation reactions. This review summarizes the recent developments in copper-catalyzed carboxylation reactions with CO 2 , the contents of which are divided into five parts based on the type of the substrates or products: organic halides and their surrogates, CÀ C double bonds, CÀ C triple bonds, CÀ H bonds and the synthesis of heterocycles.

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