Synthesis of N-picolylcarboxamides via palladium-catalysed aminocarbonylation of iodobenzene and iodoalkenes

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

doi:10.1016/j.tet.2013.11.087

Cited by 18 publications

(7 citation statements)

References 43 publications

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“…The chemoselectivity towards the doubly carbonylated product reached 94% at 40 bar of CO pressure when 3-picolylamine was employed as N-nucleophile. No double carbonylation was observed, however, for the iodoalkene substrates [58]. Similar dependence upon the substrate was observed when iodopyridine model compounds were aminocarbonylated with various primary and secondary amines [59].…”

Section: Reactions In Conventional Solventssupporting

confidence: 60%

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 Solventssupporting

confidence: 60%

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

2022

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“…3- and 4-picolylamine ( q , r ) showed similar behavior as nucleophile o , because high reactivity and perfect 2-ketocarboxamide selectivity were observed (entries 17, 18). As we described previously [ 75 ], 2-picolylamine ( p ) showed lower reactivity than q and r , because its good coordination ability to the central metal could decrease the reaction rate of the oxidative step of the catalytic cycle. In this way, complete conversion was achieved in just 14 h and the selectivity towards the corresponding ketoamide ( 3p ) was decreased to 66% (entry 16).…”

Section: Resultsmentioning

confidence: 97%

Highly Selective Synthesis of 6-Glyoxylamidoquinoline Derivatives via Palladium-Catalyzed Aminocarbonylation

et al. 2021

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The aminocarbonylation of 6-iodoquinoline has been investigated in the presence of large series of amine nucleophiles, providing an efficient synthetic route for producing various quinoline-6-carboxamide and quinoline-6-glyoxylamide derivatives. It was shown, after detailed optimization study, that the formation of amides and ketoamides is strongly influenced by the reaction conditions. Performing the reactions at 40 bar of carbon monoxide pressure in the presence of Pd(OAc)2/2 PPh3, the corresponding 2-ketocarboxamides were formed as major products (up to 63%). When the monodentate triphenylphosphine was replaced by the bidentate XantPhos, the quinoline-6-carboxamide derivatives were synthesized almost exclusively under atmospheric conditions (up to 98%). The isolation and characterization of the new carbonylated products of various structures were also accomplished. Furthermore, the structure of three new mono- and double-carbonylated compounds were unambiguously established by using a single-crystal XRD study.

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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 N-picolylcarboxamides via palladium-catalysed aminocarbonylation of iodobenzene and iodoalkenes

Cited by 18 publications

References 43 publications

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

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

Highly Selective Synthesis of 6-Glyoxylamidoquinoline Derivatives via 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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