Facile synthesis of 1,8-naphthalimides in palladium-catalysed aminocarbonylation of 1,8-diiodo-naphthalene

Takács, Attila; Ács, Pongrác; Kollár, László

doi:10.1016/j.tet.2007.10.026

Cited by 33 publications

(12 citation statements)

References 18 publications

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“…It has to be noted that a similar imide formation was already investigated with primary monoamines. [9] The aminocarbonylation of 6 was also carried out with (R ax / S ax )-BINAM in the presence of the chiral ligands above ((2S,3S)-CHIRAPHOS, (2S,4S)-BDPP, (R ax )-BINAP) Practically racemic mixtures were obtained in all cases except to BDPP, where slight enantiomeric enrichment of 7 (R ax )-7/(S ax )-7 = 47/53) can be achieved. As above, no perfect base-line separation of the two enantiomers of 8 with chiral HPLC could be achieved.…”

Section: Aminocarbonylation Of 18-diiodonaphthalene (6) In the Presementioning

confidence: 99%

Synthesis of Axially Chiral Carboxamides via Aminocarbonylation of Aryl and Vinyl Iodides with 2,2’‐Diamino‐1,1’‐binaphthalene in the Presence of Palladium Catalysts

et al. 2020

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Palladium‐catalysed aminocarbonylation of iodobenzene and 1‐iodocyclohexene with both enantiomerically pure and racemic 2,2’‐diamino‐1,1’‐binaphthalene (BINAM) as N‐nucleophile was carried out. The mono‐ and dicarboxamide enantiomers possessing axial chirality were synthesised using (Sax)‐BINAM. In the possession of these reference compounds the partial chiral kinetic resolution of racemic BINAM was carried out using various optically active bidentate ligands such as (2S,4S)‐BDPP, (2S,3S)‐CHIRAPHOS and (R)‐BINAP. It was revealed by chiral HPLC measurements that up to 10 % enantiomeric excess of carboxamides can be achieved in this way. Although with low enantioselection, enantioselectve aminocarbonylation was carried out for the first time.

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Section: Aminocarbonylation Of 18-diiodonaphthalene (6) In the Presementioning

confidence: 99%

Synthesis of Axially Chiral Carboxamides via Aminocarbonylation of Aryl and Vinyl Iodides with 2,2’‐Diamino‐1,1’‐binaphthalene in the Presence of Palladium Catalysts

et al. 2020

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“…Similarly Kollar et al. reported the synthesis of 1,8‐naphthalimides from 1,8‐diiodonaphthalene, a primary amine and CO using a palladium phosphine catalytic system 10. Recently, Alper et al.…”

Section: Introductionmentioning

confidence: 96%

Enantioselective Cascade Michael Addition/Cyclization Reactions of 3‐Nitro‐2H‐Chromenes with 3‐Isothiocyanato Oxindoles: Efficient Synthesis of Functionalized Polycyclic Spirooxindoles

Tan

Yang

et al. 2014

Chemistry A European J

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An unprecedented Zn(OTf)2-catalyzed asymmetric Michael addition/cyclization cascade of 3-nitro-2H-chromenes with 3-isothiocyanato oxindoles has been disclosed. This transformation provides an efficient access to various synthetically important polycyclic spirooxindoles in a highly stereoselective manner under mild conditions (72–99% yields, up to >95:5 d.r. and >99% ee). The reaction leads to the formation of three consecutive stereocenters, including 1,3-nonadjacent tetrasubstituted carbon stereocenters, in a single operation. A bifunctional activation model of the chiral Zn(OTf)2/bis(oxazoline) complex was proposed based on control experiments, wherein the ZnII moiety serves as a Lewis acid and the N atom of the free NH group acts as a Lewis base by a hydrogen-bonding interaction.

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“…[9] Similarly Kollar et al reported the synthesis of 1,8-naphthalimides from 1,8-diiodonaphthalene, a primary amine and CO using a palladium phosphine catalytic system. [10] Recently, Alper et al has further extended the same protocol using a phosphonium salt ionic liquid. [11] Some recent approaches for phthalimide synthesis include the Ru 3 (CO) 12 -catalyzed C À H bond activation of aromatic amides [12] and [RuH 2 A C H T U N G T R E N N U N G (PPh 3 ) 4 ]-catalyzed synthesis of phthalimides using diols.…”

Section: Introductionmentioning

confidence: 99%

Palladium on Carbon: An Efficient, Heterogeneous and Reusable Catalytic System for Carbonylative Synthesis of N‐Substituted Phthalimides

et al. 2011

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The application of palladium on carbon (Pd/C) as a heterogeneous recyclable catalyst was investigated for the double carbonylation of o-dihaloarenes with amines providing excellent yield of Nsubstituted phthalimides in shorter reaction time as compared to earlier reported homogeneous protocols. Furthermore, the scope of the developed protocol was applied for the synthesis N-substituted phthalimides from o-halobenzoates and o-halobenzoic acid via a single step carbonylative cyclization reaction. The developed methodology describes an efficient one-step approach for the synthesis of an important class of heterocycles and tolerates a wide variety of functional groups. It circumvents the use of phosphine ligands with an additional advantage of catalyst recyclability for up to eight consecutive cycles.

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Facile synthesis of 1,8-naphthalimides in palladium-catalysed aminocarbonylation of 1,8-diiodo-naphthalene

Cited by 33 publications

References 18 publications

Synthesis of Axially Chiral Carboxamides via Aminocarbonylation of Aryl and Vinyl Iodides with 2,2’‐Diamino‐1,1’‐binaphthalene in the Presence of Palladium Catalysts

Synthesis of Axially Chiral Carboxamides via Aminocarbonylation of Aryl and Vinyl Iodides with 2,2’‐Diamino‐1,1’‐binaphthalene in the Presence of Palladium Catalysts

Enantioselective Cascade Michael Addition/Cyclization Reactions of 3‐Nitro‐2H‐Chromenes with 3‐Isothiocyanato Oxindoles: Efficient Synthesis of Functionalized Polycyclic Spirooxindoles

Palladium on Carbon: An Efficient, Heterogeneous and Reusable Catalytic System for Carbonylative Synthesis of N‐Substituted Phthalimides

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