Tri(1‐naphthyl)phosphine as a ligand in palladium‐free Sonogashira cross‐coupling of arylhalogenides with acetylenes

Govdi, Anastasia I.; Vasilevsky, S. F.; Малышева, С. Ф.; Kazheva, Olga N.; D’yachenko, O. A.; Kuimov, Vladimir A.

doi:10.1002/hc.21443

Cited by 9 publications

(2 citation statements)

References 33 publications

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“…Another common problem is a complicated purification of a reaction product, caused by a high solubility of phosphines and their oxides in organic solvents. To address these challenges, apart from phosphines, 10,37 numerous N , N -, 38 N , O -, 39 and O , O -chelators 40 as well as other alternative ligands 41 have been proposed for the Cu-catalyzed Sonogashira coupling. A number of ligand-free protocols have been also reported.…”

Section: Resultsmentioning

confidence: 99%

Copper-catalyzed deacetonative Sonogashira coupling

et al. 2022

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Section: Resultsmentioning

confidence: 99%

Copper-catalyzed deacetonative Sonogashira coupling

et al. 2022

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“…Replacing the triphenylphosphine ligands with tri-1-naphthylphosphine would then enable the obtention of the PdCl 2 (PN 3 ) 2 complex which has a molecular weight of 1001 g mol −1 that could theoretically be better separated. It is worth noticing that this new catalyst has already been used in Sonogashira coupling reactions [ 113 , 114 ]. In addition, tri-1-naphthylphosphine is commercially available at a reasonable price from different chemical suppliers which can be quite interesting for industrial use.…”

Section: State-of-the-art Catalyst Recovery By Membrane Processesmentioning

confidence: 99%

Recovery of Homogeneous Platinoid Catalysts from Pharmaceutical Media: Review on the Existing Treatments and the Perspectives of Membrane Processes

Magne,

Carretier,

Ubiera Ruiz

et al. 2023

Membranes

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Catalyst recovery is a major challenge for reaching the objectives of green chemistry for industry. Indeed, catalysts enable quick and selective syntheses with high reaction yields. This is especially the case for homogeneous platinoid catalysts which are almost indispensable for cross-coupling reactions often used by the pharmaceutical industry. However, they are based on scarce, expensive, and toxic resources. In addition, they are quite sensitive and degrade over time at the end of the reaction. Once degraded, their regeneration is complex and hazardous to implement. Working on their recovery could lead to highly effective catalytic chemistries while limiting the environmental and economic impacts of their one-time uses. This review aims to describe and compare conventional processes for metal removal while discussing their advantages and drawbacks considering the objective of homogeneous catalyst recovery. Most of them lead to difficulty recycling active catalysts due to their ability to only treat metal ions or to chelate catalysts without the possibility to reverse the mechanism. However, membrane processes seem to offer some perspectives with limiting degradations. While membranes are not systematically the best option for recycling homogeneous catalysts, current development might help improve the separation between pharmaceutical active ingredients and catalysts and enable their recycling.

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Carbazole‐Based N‐Heterocyclic Carbenes for the Promotion of Copper‐Catalyzed Palladium‐Free Homo‐/Hetero‐Coupling of Alkynes and Sonogashira Reactions

et al. 2020

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Alkynes are useful synthetic building blocks that occur in many naturally occurring molecules and have the potential to be easily modified for further natural products and drug synthesis applications. Given the‐versatility of the alkyne functionality,‐various synthetic methods (mostly palladium‐based) are known in the literature, allowing the installation to take place under different reaction conditions. A single catalytic system (without Pd) however, if developed could provide a single point solution for the installation of the alkyne moiety and keeping this in mind, we report herein a highly active palladium‐free Cu/carbazole‐based NHC catalyst system allowing homocoupling and heterocoupling of alkynes at ambient temperature. Using a combination of Cu/NHC‐catalyzed homocoupling/deprotection/heterocoupling sequence tetraynes have also been synthesized in good yields. The Cu/NHC catalyst system was also able to catalyze a palladium‐free Sonogashira reaction of synthetically useful nucleosides.

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Tri(1‐naphthyl)phosphine as a ligand in palladium‐free Sonogashira cross‐coupling of arylhalogenides with acetylenes

Cited by 9 publications

References 33 publications

Copper-catalyzed deacetonative Sonogashira coupling

Copper-catalyzed deacetonative Sonogashira coupling

Recovery of Homogeneous Platinoid Catalysts from Pharmaceutical Media: Review on the Existing Treatments and the Perspectives of Membrane Processes

Carbazole‐Based N‐Heterocyclic Carbenes for the Promotion of Copper‐Catalyzed Palladium‐Free Homo‐/Hetero‐Coupling of Alkynes and Sonogashira Reactions

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