Synthesis of novel 13α-18-nor-16-carboxamido steroids via a palladium-catalyzed aminocarbonylation reaction

Szánti-Pintér, Eszter; Csók, Zsolt; Berente, Zoltán; Kollár, László; Skoda‐Földes, Rita

doi:10.1016/j.steroids.2013.08.011

Cited by 6 publications

(6 citation statements)

References 32 publications

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“…Catalytic experiments resumed in Table were carried out at high CO pressure with the goal to compare with previously reported works . In all entries, amide ( b ) is the favoured product.…”

Section: Effect Of the Auxiliary Ligand And Low Co Pressure In The Ammentioning

confidence: 99%

“…After purification, single monocrystals from the oxide of L 1 ligand were obtained from the washing mixture and resolved via X-ray diffraction ( Figure 2; Table 1). P^N ligands are known to be air-sensitive in solution, which SCHEME 1 Iodobenzene aminocarbonylation catalysed by palladium (II) complexes, which yield amides a and b as major products Pd-C31 1.806 (8) leads to oxidation of the phosphine group. The resolved structure shows that one diphenylphosphine group linked the amine moiety of the pyridine-derived substrate through nucleophilic substitution, which was the main goal.…”

Section: Synthesismentioning

confidence: 99%

“…[20] Catalytic experiments resumed in Table 3 were carried out at high CO pressure with the goal to compare with previously reported works. [7][8][9][17][18][19][20] In all entries, amide (b) is the favoured product. To establish what the influence of the CO pressure is in this behaviour, two in situ systems using ligands L 3 and L 4 (both with high activities and chemoselectivities at high CO pressure) were studied at the minimum pressure allowed by the reactors (approximately 5 bar).…”

Section: Figure 4 Mechanism Of Aminocarbonylation Reactionmentioning

confidence: 99%

“…[4][5][6][7] For example, 13α-steroid amide products that are pharmacologically significant have been synthesized using homogeneous palladium catalysts. [8,9] For this reaction, palladium (II) catalysts formed in situ are currently used by reaction of a palladium (II) precursor and a ligand such as PPh 3 . Palladium (II) complexes containing bidentate P^P ligands that have been studied as catalysts in aminocarbonylation show high activity but in a longer time compared with a standard catalyst Pd (II)/PPh 3 , as the ligand stabilizes the Pd (0)/ P^P species too much, hindering the oxidative addition of the substrate.…”

Section: Introductionmentioning

confidence: 99%

“…These aromatic amides can be used as synthesis blocks in the polymerization of products of pharmacological interest . For example, 13α‐steroid amide products that are pharmacologically significant have been synthesized using homogeneous palladium catalysts …”

Section: Introductionmentioning

confidence: 99%

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New palladium (II) complexes containing phosphine‐nitrogen ligands and their use as catalysts in aminocarbonylation reaction

Aranda

Moya

Vega

et al. 2019

Applied Organom Chemis

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Aminocarbonylation of aryl halides, homogeneously catalysed by palladium, is an efficient method that can be employed for obtaining amides for pharmaceutical and synthetic applications. In this work, palladium (II) complexes containing P^N ligands were studied as catalysts in the aminocarbonylation of iodobenzene in the presence of diethylamine. Two types of systems were used: a palladium (II) complex formed in situ; and one prepared prior to the catalytic reaction. In general, the palladium complexes studied achieved high conversions in an average reaction time of less than 2 hr, which is less than that for the standard system (Pd (II)/PPh3) used. The pre‐synthesized complexes were faster than their in situ counterparts, as the latter require an induction time to form the Pd/P^N species. The structure and electronic properties of the ligand P^N can influence both the activity and the selectivity of the reaction, stabilizing the acyl‐palladium intermediates formed in a better manner.

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“…Catalytic experiments resumed in Table were carried out at high CO pressure with the goal to compare with previously reported works . In all entries, amide ( b ) is the favoured product.…”

Section: Effect Of the Auxiliary Ligand And Low Co Pressure In The Ammentioning

confidence: 99%

Section: Synthesismentioning

confidence: 99%

Section: Figure 4 Mechanism Of Aminocarbonylation Reactionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

New palladium (II) complexes containing phosphine‐nitrogen ligands and their use as catalysts in aminocarbonylation reaction

Aranda

Moya

Vega

et al. 2019

Applied Organom Chemis

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Palladium‐Catalyzed Alkoxy‐ and Aminocarbonylation of α‐Halomethyl Oxime Ethers: Synthesis of 1,3‐Alkoxyimino Esters and 1,3‐Alkoxyimino Amides

2014

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Carbon Monoxide as C1 Building Block in Fine Chemical Synthesis^†

Carrilho,

Calvete,

Mikle

et al. 2023

Chin. J. Chem.

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Carbon monoxide (CO) has become one of the most relevant and versatile renewable C1 building blocks for chemical synthesis, especially in the fine chemicals industry, due to the development of efficient and selective catalysts for its activation. In this review, we present a comprehensive critical analysis of the last 10 years literature on the use of CO as a renewable feedstock for fine chemicals production. The review is organized by type of catalytic reaction, namely alkene and alkyne carbonylation, hydroformylation, carbonylation of aryl halides, carbonylative cross‐coupling and C–H carbonylation. Notable examples of the synthesis of relevant building blocks and/or known pharmaceuticals are highlighted. Emphasis is placed on examples of utilizing CO as the C1 building block in one or more catalytic steps. The catalyst used and the reaction conditions are consistently presented throughout all of the examples.This article is protected by copyright. All rights reserved.

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Synthesis of novel 13α-18-nor-16-carboxamido steroids via a palladium-catalyzed aminocarbonylation reaction

Cited by 6 publications

References 32 publications

New palladium (II) complexes containing phosphine‐nitrogen ligands and their use as catalysts in aminocarbonylation reaction

New palladium (II) complexes containing phosphine‐nitrogen ligands and their use as catalysts in aminocarbonylation reaction

Palladium‐Catalyzed Alkoxy‐ and Aminocarbonylation of α‐Halomethyl Oxime Ethers: Synthesis of 1,3‐Alkoxyimino Esters and 1,3‐Alkoxyimino Amides

Carbon Monoxide as C1 Building Block in Fine Chemical Synthesis^†

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Synthesis of novel 13α-18-nor-16-carboxamido steroids via a palladium-catalyzed aminocarbonylation reaction

Cited by 6 publications

References 32 publications

New palladium (II) complexes containing phosphine‐nitrogen ligands and their use as catalysts in aminocarbonylation reaction

New palladium (II) complexes containing phosphine‐nitrogen ligands and their use as catalysts in aminocarbonylation reaction

Palladium‐Catalyzed Alkoxy‐ and Aminocarbonylation of α‐Halomethyl Oxime Ethers: Synthesis of 1,3‐Alkoxyimino Esters and 1,3‐Alkoxyimino Amides

Carbon Monoxide as C1 Building Block in Fine Chemical Synthesis†

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Product

Resources

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Carbon Monoxide as C1 Building Block in Fine Chemical Synthesis^†