Aminocarbonylation

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Xiaofeng Wu - One of the best experts on this subject based on the ideXlab platform.

Giancarlo Cravotto - One of the best experts on this subject based on the ideXlab platform.

László Kollár - One of the best experts on this subject based on the ideXlab platform.

  • High-yielding synthesis of N-triazolyl carboxamides via palladium-catalysed Aminocarbonylation
    Tetrahedron, 2017
    Co-Authors: Máté Gergely, Borbála Boros, László Kollár
    Abstract:

    Abstract Aminocarbonylation of alkenyl and aryl iodides in the presence of 4-amino-4H-1,2,4-triazole as N-nucleophile was carried out in the presence of palladium catalysts. Both types of substrates have shown high chemoselectivity toward carboxamides, i.e. practically no double carbon monoxide insertion resulting in 2-ketocarboxamides took place. The results have been rationalised on the basis of mechanistic aspects of Aminocarbonylation.

  • Palladium-catalysed Aminocarbonylation of diiodopyridines
    Tetrahedron, 2017
    Co-Authors: Attila Takács, Georgina Márta Varga, Johanna Kardos, László Kollár
    Abstract:

    Abstract The Aminocarbonylation of 2,5- and 2,3-diiodopyridine, as well as 2-chloro-3,4-diiodopyridine with carbon monoxide and various primary and secondary amines was carried out using palladium-catalysed Aminocarbonylation. The formation of the products containing carboxamide and ketocarboxamide functionalities was accompanied by the formation of imides when ortho-diiodo compounds were used as substrates. In spite of several possible reaction pathways, most of the products were synthesised as major product in yields of synthetic interest by the appropriate modification of the reaction conditions.

  • Synthesis of bornene-2,2′-diamino-1,1′-binaphthalene conjugates in palladium-catalysed Aminocarbonylations
    Tetrahedron-asymmetry, 2016
    Co-Authors: Gábor Mikle, Borbála Boros, László Kollár
    Abstract:

    Abstract Palladium-catalysed Aminocarbonylation of a terpenoic iodoalkene (2-iodo-bornene) model compound with both enantiomerically pure and racemic 2,2′-diamino-1,1′-binaphthalene (BINAM) as the N -nucleophile was carried out. All of the diastereoisomers of the monocarboxamide ( N -bornenyl carboxamide) and dicarboxamide ( N , N ′-dinorbornenylcarboxamide) derivatives were synthesised. The diastereoselectivities of the Aminocarbonylation were investigated in both cases: either racemic BINAM was used as the N -nucleophile in the Aminocarbonylation of enantiomerically pure 2-iodobornene or racemic iodobornene was aminocarbonylated with enantiomerically pure BINAM with moderate diastereoselectivities. In this way, all possible diastereoisomers of binaphthalene–bornene conjugates were synthesised in moderate to high yields by asymmetric (diastereoselective) Aminocarbonylation.

  • Synthesis of amino-substituted pyridylglyoxylamides via palladium-catalysed Aminocarbonylation
    Tetrahedron, 2016
    Co-Authors: Gyöngyi Szőke, Andrea Petz, Attila Takács, Zoltán Berente, László Kollár
    Abstract:

    Abstract Palladium-catalysed Aminocarbonylation of iodopyridine model compounds (4-amino-3-iodopyridine and 3-amino-4-iodopyridine) with various primary and secondary amines including amino acid methyl esters was carried out. The two substrates behave in a completely different manner under Aminocarbonylation conditions: 4-amino-3-iodopyridine gave the corresponding 2-ketocarboxamides (nicotinamide analogues) due to double carbon monoxide insertion, while 3-amino-4-iodopyridine reacted as a bifunctional substrate resulting in a dicarboxamide containing two pyridyl moieties.

  • 4‐Amino‐TEMPO as N‐Nucleophile in Palladium‐Catalyzed Aminocarbonylation
    Journal of Heterocyclic Chemistry, 2016
    Co-Authors: Máté Gergely, Attila Takács, László Kollár
    Abstract:

    Palladium-catalyzed Aminocarbonylation of iodobenzene and iodoalkenes (1-iodocyclohexene, 4-tert-butyl-1- iodocyclohexene, α-iodostyrene, 17-iodoandrost-16-ene) was carried out using a free radical (4-amino-TEMPO) for the first time. Its reduced form (4-amino-2,2,6,6-tetramethylpiperidine) was also used as N-nucleophile. The free radical was partially reduced under Aminocarbonylation conditions; however, the isolation of carbonylated products bearing a stable radical moiety was successfully accomplished. It was proved that the reduction of the 1-oxyl functionality took place to higher extent when more severe conditions (40 bar CO pressure) were used. The mixture of carboxamide and 2-ketocarboxamide products was obtained using iodobenzene because of single and double carbon monoxide insertion, respectively. In turn, carboxamide derivatives were formed exclusively when iodoalkenes were used as substrates.

Emanuela Calcio Gaudino - One of the best experts on this subject based on the ideXlab platform.

Jinheng Li - One of the best experts on this subject based on the ideXlab platform.