Synthesis of 2-naphthylacrylamides and 2-naphthylacrylates via homogeneous catalytic carbonylation of 1-iodo-1-naphthylethene derivatives

Takács, Attila; Farkas, Roland; Petz, Andrea; Kollár, László

doi:10.1016/j.tet.2009.04.056

Cited by 9 publications

(3 citation statements)

References 11 publications

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“…Two highly reactive iodoalkenes, that is 1-iodo-1-(2-naphthyl)ethene and 1-iodo-1-(1naphthyl)ethene) were prepared and used as substrates in Pd-catalyzed aminocarbonylation with various N-nucleophiles. The corresponding N-substituted naphthylacrylamides were produced chemoselectively in nearly quantitative yields [51].…”

Section: Reactions In Conventional Solventsmentioning

confidence: 99%

27 Years of Catalytic Carbonylative Coupling Reactions in Hungary (1994–2021)

2022

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Palladium-catalyzed carbonylation reactions, in the presence of nucleophiles, serve as very potent tools for the conversion of aryl and alkenyl halides or halide equivalents to carboxylic acid derivatives or to other carbonyl compounds. There are a vast number of applications for the synthesis of simple building blocks as well as for the functionalization of biologically important skeletons. This review covers the history of carbonylative coupling reactions in Hungary between the years 1994 and 2021.

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Section: Reactions In Conventional Solventsmentioning

confidence: 99%

27 Years of Catalytic Carbonylative Coupling Reactions in Hungary (1994–2021)

2022

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“…One of these reactions is aminocarbonylation, which has great importance concerning the synthesis of simple building blocks and the functionalization of biologically important skeletons. Carboxamides can be synthesized from easily available starting materials with aminocarbonylation, although the conventional carboxylic acid−carboxylic halide−carboxamide route is difficult to prepare because it has no notable yield in the implementation [ 29 , 30 ]. Moreover, our research group has been investigating this reaction in the conventional solvent DMF for years [ 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 ], and thanks to the ascertainments of the groups from Skrydstrup [ 40 ] and Mika [ 41 , 42 , 43 ], our interest has been turned to the investigation of green solvents.…”

Section: Introductionmentioning

confidence: 99%

Alkyl Levulinates and 2-Methyltetrahydrofuran: Possible Biomass-Based Solvents in Palladium-Catalyzed Aminocarbonylation

et al. 2023

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In this research, ethyl levulinate, methyl levulinate, and 2-methyltetrahydrofuran as bio-derived hemicellulose-based solvents were applied as green alternatives in palladium-catalyzed aminocarbonylation reactions. Iodobenzene and morpholine were used in optimization reactions under different conditions, such as temperatures, pressures, and ligands. It was shown that the XantPhos ligand had a great influence on conversion (98%) and chemoselectivity (100% carboxamide), compared with the monodentate PPh3. Following this study, the optimized conditions were used to extend the scope of substrates with nineteen candidates (various para-, ortho-, and meta-substituted iodobenzene derivatives and iodo-heteroarenes), as well as eight different amine nucleophiles.

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“…18,19 Recently, the palladium-catalyzed aminocarbonylation of 5-iodoindole and 7-iodoindole derivatives with various primary and secondary amines has been reported. 20 Kollár described efficient aminocarbonylation of iodoalkenes and iodoaromatic with primary and secondary amines, catalyzed by Pd(OAc) 2 with addition of PPh 3 [21][22][23][24][25][26] . The same catalytic system has been used in aminocarbonylation of iodoalkenes and iodobenzene with diethyl α-aminobenzyl-phosphonate 27 and aminoacid methyl esters in ionic liquids.…”

Section: Introductionmentioning

confidence: 99%

In situ generated Pd(0) nanoparticles stabilized by bis(aryl)acenaphthenequinone diimines as catalysts for aminocarbonylation reactions in water

Wójcik

Rosar

Gniewek

et al. 2016

Journal of Molecular Catalysis A: Chemical

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Aminocarbonylation of aryl iodides with aromatic and aliphatic amines, leading to formation of the corresponding amides, was efficiently carried out in water under 1 atm of CO using palladium nanoparticles (Pd NPs) formed in situ from [PdCl2(Ar2-BIAN)] complexes. The role of Ar2-BIAN ligands in the stabilization of Pd NPs was evidenced. The nature of the catalytically active species was confirmed by poisoning experiments, which highlighted that the catalyst is actually in the form of Pd NPs rather than soluble palladium complexes. In the aminocarbonylation of iodobenzene with substituted anilines good yields of amides were obtained, although the activity was depleted by the presence of substituents in the ortho positions of the aniline. On the other hand, in the reaction with aliphatic amines α-ketoamides were formed in addition to the amides. The selectivity towards α-ketoamides was increased by increasing the CO pressure to 10 atm, at equimolar amounts of PhI and amine. Pd NPs were successfully recovered after the catalytic reaction and recycled in five subsequent runs with only a marginal loss of activity after the fourth cycle

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Synthesis of 2-naphthylacrylamides and 2-naphthylacrylates via homogeneous catalytic carbonylation of 1-iodo-1-naphthylethene derivatives

Cited by 9 publications

References 11 publications

27 Years of Catalytic Carbonylative Coupling Reactions in Hungary (1994–2021)

27 Years of Catalytic Carbonylative Coupling Reactions in Hungary (1994–2021)

Alkyl Levulinates and 2-Methyltetrahydrofuran: Possible Biomass-Based Solvents in Palladium-Catalyzed Aminocarbonylation

In situ generated Pd(0) nanoparticles stabilized by bis(aryl)acenaphthenequinone diimines as catalysts for aminocarbonylation reactions in water

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