Palladium‐Catalyzed Carbonylative α‐Arylation for Accessing 1,3‐Diketones

Gøgsig, Thomas M.; Taaning, Rolf H.; Lindhardt, Anders T.; Skrydstrup, Troels

doi:10.1002/anie.201107494

Cited by 95 publications

(36 citation statements)

References 51 publications

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“…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 . A recent work demonstrated the ability of 9‐methyl‐9H‐fluorene‐9‐carbonyl chloride (named “COgen” upon commercialisation) to release CO via a palladium‐catalysed decarbonylation reaction performed at 80°C, Scheme . 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: Co‐releasing Molecules (Co‐rms)mentioning

confidence: 99%

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%

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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“…and Heck et al., palladium‐catalyzed carbonylation, an efficient pathway for the constructing of carbonyl‐containing skeletons, has become a versatile tool in creating chemical diversity . Long‐lasting interests have been focused on the chemoselectivity of the palladium‐catalyzed carbonylation of one nucleophile bearing two nucleophilic sites (Scheme ), for example, the chemoselective carbonylation of aminophenols (alkoxycarbonylation vs. aminocarbonylation, Scheme a),– the selective carbonylative synthesis of 1,3‐diketones and vinylbenzoates from ketones with α‐hydrogen atoms (carbonylative α‐arylation vs. O ‐benzoylation, Scheme b)– and the base‐controlled tunable synthesis of linear‐ and angular‐fused quinazolinones with 2‐aminopyridine (two different nucleophilic nitrogen centers, Scheme c) …”

Section: Introductionmentioning

confidence: 99%

Ligand‐ and Solvent‐Tuned Chemoselective Carbonylation of Bromoaryl Triflates

Shen

Wei

Jiao

et al. 2017

Chemistry A European J

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The palladium-catalyzed chemoselective carbonylation of bromoaryl triflates is reported. The selective C-Br bond versus C-OTf (OTf=triflate) bond functionalization can be remarkably tuned by the combination of the ligand [4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) vs. 1,1'-bis(diphenylphosphino)ferrocene (DPPF)] and the solvent (toluene vs. DMSO). The respective ligand and solvent effects are rationalized by DFT calculations. In contrast, the monodentate ligands BuPAd and tBu P prefer the selective C-Br bond activation and are solvent insensitive.

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“…The first example of this is shown in Scheme 18A. Preforming the enolate with NaHMDS as the base followed by Pd‐catalyzed carbonylative coupling to an aryl iodide allowed for the isolation of the 13 C‐labeled 1,3‐diketone 71 . Having a MOM‐protected phenol installed on the aryl ring ortho to the acyl group provided access to the 13 C‐labeled flavone‐derivative 72 through a Brønsted acid‐mediated cyclization.…”

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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Palladium‐Catalyzed Carbonylative α‐Arylation for Accessing 1,3‐Diketones

Cited by 95 publications

References 51 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

Ligand‐ and Solvent‐Tuned Chemoselective Carbonylation of Bromoaryl Triflates

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

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Palladium‐Catalyzed Carbonylative α‐Arylation for Accessing 1,3‐Diketones

Cited by 95 publications

References 51 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

Ligand‐ and Solvent‐Tuned Chemoselective Carbonylation of Bromoaryl Triflates

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