Low-cost instant CO generation at room temperature using formic acid, mesyl chloride and triethylamine

Veryser, Cedrick; Mileghem, Seger Van; Egle, Brecht; Gilles, Philippe; Borggraeve, Wim M. De

doi:10.1039/c6re00006a

Cited by 35 publications

(37 citation statements)

References 29 publications

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“…Carbon monoxide‐releasing molecules (CO‐RMs) are compounds able to release carbon monoxide under specific conditions. Past studies have shown the application of CO‐RMs in medicine as therapeutic agents and in synthetic chemistry as CO trapping‐releasing agents . The synthesis of metal carbonyl complexes, such as rhuthenium‐CO and copper‐CO complexes, and their application as in situ CO‐releasing molecules have rapidly increased .…”

Section: Co‐releasing Molecules (Co‐rms)mentioning

confidence: 99%

“…Past studies have shown the application of CO-RMs in medicine as therapeutic agents 74,75 and in synthetic chemistry as CO trapping-releasing agents. 69,[76][77][78][79][80][81][82][83] The synthesis of metal carbonyl complexes, such as rhuthenium-CO and copper-CO complexes, and their application as in situ CO-releasing molecules have rapidly increased. 69,[84][85][86][87][88] These complexes are able to release CO under physiological conditions 84 or by addition of a competing ligand.…”

Section: Mechanism Of 11 C-carbonylation With [ 11 C]comentioning

confidence: 99%

“…90 Many other CO production methodologies utilising aldehydes, carbamoylsilane, carbamoylstannanes, formic acid, and its derivatives have been developed and applied to the synthesis of carbonyl functionalised molecules. 79,80,91 A recent work demonstrated the ability of 9methyl-9H-fluorene-9-carbonyl chloride (named "COgen" upon commercialisation) to release CO via a palladiumcatalysed decarbonylation reaction performed at 80°C, Scheme 17. 93,94 The combination of this CO-releasing process with a CO-consuming reaction in an isolated 2-chamber system enabled a high trapping of the produced CO.…”

Section: Mechanism Of 11 C-carbonylation With [ 11 C]comentioning

confidence: 99%

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Recent progress in [¹¹C]carbon dioxide ([¹¹C]CO₂) and [¹¹C]carbon monoxide ([¹¹C]CO) chemistry

Taddei

Gee

2018

Labelled Comp Radiopharmac

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[ 11 C]Carbon dioxide ([ 11 C]CO 2 ) and [ 11 C]carbon monoxide ([ 11 C]CO) are 2 attractive precursors for labelling the carbonyl position (C═O) in a vast range of functionalised molecules (eg, ureas, amides, and carboxylic acids). The development of radiosynthetic methods to produce functionalised 11 C‐labelled compounds is required to enhance the radiotracers available for positron emission tomography, molecular, and medical imaging applications. Following a brief summary of secondary 11 C‐precursor production and uses, the review focuses on recent progress with direct 11 C‐carboxylation routes with [ 11 C]CO 2 and 11 C‐carbonylation with [ 11 C]CO. Novel approaches to generate [ 11 C]CO using CO‐releasing molecules (CO‐RMs), such as silacarboxylic acids and disilanes, applied to radiochemistry are described and compared with standard [ 11 C]CO production methods. These innovative [ 11 C]CO synthesis strategies represent efficient and reliable [ 11 C]CO production processes, enabling the widespread use of [ 11 C]CO chemistry within the wider radiochemistry community.

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Section: Co‐releasing Molecules (Co‐rms)mentioning

confidence: 99%

Section: Mechanism Of 11 C-carbonylation With [ 11 C]comentioning

confidence: 99%

Section: Mechanism Of 11 C-carbonylation With [ 11 C]comentioning

confidence: 99%

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Recent progress in [¹¹C]carbon dioxide ([¹¹C]CO₂) and [¹¹C]carbon monoxide ([¹¹C]CO) chemistry

Taddei

Gee

2018

Labelled Comp Radiopharmac

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“…We investigated the activity of 12‐G 1 for carbonylative coupling with ex situ generated CO (Scheme B). In a double‐chamber reactor using the technology developed by the group of Skrydstrup, carbon monoxide is produced by decomposition of formic acid in the presence of triethylamine and mesyl chloride according to the procedure described by De Borggraeve et al . The use of such a device enables the handling of this deadly gas in a safe environment.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Catalytic Applications of Multi‐Walled Carbon Nanotube–Polyamidoamine Dendrimer Hybrids

Desmecht

Steenhaut

Pennetreau

et al. 2018

Chemistry A European J

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Polyamidoamine (PAMAM) dendrimers were covalently immobilized on multi-walled carbon nanotubes (MWNT) by two "grafting to" strategies. We demonstrate the existence of non-covalent interactions between the two components but outline the superiority of our two grafting approaches, namely xanthate and click chemistry. MWNT surfaces were functionalized with activated ester and propargylic moieties prior to their reaction with PAMAM or azido-PAMAM dendrimers, respectively. The grafting of PAMAM generations 0 to 3 was evaluated with X-ray photoelectron spectroscopy (XPS), thermogravimetric analysis (TGA), and transmission electron microscopy (TEM). The versatility of our hybrids was demonstrated by post-functionalization sequences involving copper alkyne-azide cycloaddition (CuAAC). We synthesized homogeneous supported iridium complexes at the extremities of the dendrimers. In addition, our materials were used as templates for the encapsulation of Pd nanoparticles (NPs), validating our nanocomposites for catalytic applications. The palladium-based catalyst was active for carbonylative coupling over five consecutive runs without loss of activity.

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“…Veryser et al reported on a related strategy by using mesyl chloride for activating formic acid instead of acetic anhydride. The CO‐liberation was rapid under the developed conditions and could be generated ex situ by using COware for aminocarbonylations and carbonylative cyclizations, respectively. Representative examples of 13 C‐enriched compounds from these studies are depicted in Scheme 29A ( 110 and 111 ).…”

Section: C‐carbonylation Using [13c]comentioning

confidence: 99%

Recent developments in carbonylation chemistry using [¹³C]CO, [¹¹C]CO, and [¹⁴C]CO

Nielsen

Neumann

Lindhardt

et al. 2018

Labelled Comp Radiopharmac

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Carbon monoxide represents the most important C1-building block for the chemical industry, both for the production of bulk and fine chemicals, but also for synthetic fuels. Yet its toxicity and subsequently its cautious handling have limited its applications in medicinal chemistry research and in particular for the synthesis of pharmaceutically relevant molecules. Recent years have nevertheless witnessed a considerable headway on the development of carbon monoxide surrogates and reactor systems, which provide an ideal setting for performing carbonylation chemistry with stoichiometric and substoichiometric carbon monoxide. Such setups are particularly ideal for the introduction of isotope labels such as carbon-11, carbon-13, and carbon-14 into bioactive compounds. This review summarizes this growing field and examines the large number of carbonylation reactions that can be exploited for the introduction of a carbon isotope.

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Low-cost instant CO generation at room temperature using formic acid, mesyl chloride and triethylamine

Abstract: A simple and robust method for instant carbon monoxide generation at room temperature using easily accessible standard lab chemicals: formic acid, mesyl chloride and triethylamine.

Cited by 35 publications

References 29 publications

Recent progress in [¹¹C]carbon dioxide ([¹¹C]CO₂) and [¹¹C]carbon monoxide ([¹¹C]CO) chemistry

Recent progress in [¹¹C]carbon dioxide ([¹¹C]CO₂) and [¹¹C]carbon monoxide ([¹¹C]CO) chemistry

Synthesis and Catalytic Applications of Multi‐Walled Carbon Nanotube–Polyamidoamine Dendrimer Hybrids

Recent developments in carbonylation chemistry using [¹³C]CO, [¹¹C]CO, and [¹⁴C]CO

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Low-cost instant CO generation at room temperature using formic acid, mesyl chloride and triethylamine

Abstract: A simple and robust method for instant carbon monoxide generation at room temperature using easily accessible standard lab chemicals: formic acid, mesyl chloride and triethylamine.

Cited by 35 publications

References 29 publications

Recent progress in [11C]carbon dioxide ([11C]CO2) and [11C]carbon monoxide ([11C]CO) chemistry

Recent progress in [11C]carbon dioxide ([11C]CO2) and [11C]carbon monoxide ([11C]CO) chemistry

Synthesis and Catalytic Applications of Multi‐Walled Carbon Nanotube–Polyamidoamine Dendrimer Hybrids

Recent developments in carbonylation chemistry using [13C]CO, [11C]CO, and [14C]CO

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Recent progress in [¹¹C]carbon dioxide ([¹¹C]CO₂) and [¹¹C]carbon monoxide ([¹¹C]CO) chemistry

Recent progress in [¹¹C]carbon dioxide ([¹¹C]CO₂) and [¹¹C]carbon monoxide ([¹¹C]CO) chemistry

Recent developments in carbonylation chemistry using [¹³C]CO, [¹¹C]CO, and [¹⁴C]CO