Iron-catalysed quinoline synthesis <i>via</i> acceptorless dehydrogenative coupling

Yu, Keming; Chen, Qianjin; Liu, Weiping

doi:10.1039/d2qo01386j

Cited by 19 publications

(4 citation statements)

References 73 publications

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“…While the current deaminative coupling reaction shares some mechanistic features with the Friedländer quinoline synthesis, one of the distinguishing features of our proposed mechanism is the formation of an imine intermediate species 7 . To establish if imine 7 is a viable substrate, we performed the coupling reaction of a presynthesized imine substrate ( E )-2-(1-((1-phenylethyl)imino)ethyl)aniline with 1-phenylethanamine under standard conditions, which led to the product 3a in 45% yield.…”

Section: Resuts and Discussionmentioning

confidence: 92%

Benzoquinone Ligand-Enabled Ruthenium-Catalyzed Deaminative Coupling of 2-Aminoaryl Aldehydes and Ketones with Branched Amines for Regioselective Synthesis of Quinoline Derivatives

Gnyawali,

Shakenov,

Kirinde Arachchige

et al. 2024

J. Org. Chem.

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The catalytic system generated in situ from the cationic Ru− H complex [(C 6 H 6 )(PCy 3 )(CO)RuH] + BF 4 − (1) with 2,3,4,5-tetrachloro-1,2-benzoquinone (L1) was found to be highly effective for promoting the deaminative coupling reaction of 2-aminoaryl aldehydes with branched amines to form 2-substituted quinoline products. The analogous deaminative coupling reaction of 2-aminoaryl ketones with branched amines led to the regioselective formation of 2,4-disubstituted quinoline products. A number of biologically active quinoline derivatives including graveolinine and a triplex DNA intercalator have been synthesized by using the catalytic method.

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Section: Resuts and Discussionmentioning

confidence: 92%

Benzoquinone Ligand-Enabled Ruthenium-Catalyzed Deaminative Coupling of 2-Aminoaryl Aldehydes and Ketones with Branched Amines for Regioselective Synthesis of Quinoline Derivatives

Gnyawali,

Shakenov,

Kirinde Arachchige

et al. 2024

J. Org. Chem.

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“…Furthermore, we were eager to explore more synthetic utilities that the Ni-CIA catalyst has to offer, since the quinoline framework is a crucial class of heterocyclic scaffolds, which could be found in many natural products, drugs, and advanced functional materials [59][60][61]. Therefore, exploring new methods for synthesizing quinoline derivatives has become a research hotspot in the field of organic synthesis [62][63][64][65][66][67][68]. To our delight, using Ni-CIA as a catalyst, we have achieved an effective method to synthesize quinoline derivatives via borrowing hydrogen transformation.…”

Section: Catalytic Activitymentioning

confidence: 99%

Recyclable Ni-Containing Coordination Polymer as an Efficient Catalyst for the Synthesis of Oxindole and Quinoline Derivatives through the Borrowing Hydrogen Strategy

Tang

Wang

et al. 2023

Catalysts

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A coordination polymer Ni-CIA has been designed, synthesized, and characterized via Fourier transform infrared spectroscopy (FT-IR), powder X-ray diffraction (XRD), scanning electron microscopy (SEM), X-ray photoelectron spectrometry (XPS), energy-dispersive X-ray spectroscopy (EDS), and thermal gravimetric analysis (TGA). The resulting polymer reveals a slice layer stacked combination structure and good stability. Importantly, this polymer exhibited high catalytic activity for the synthesis of oxindole and quinoline derivatives via borrowing hydrogen and dehydrogenation reactions. Meanwhile, several control reactions were carried out to investigate the possible mechanisms of this transformation. Finally, the results of the recycling experiment indicate that the coordination polymer Ni-CIA could be recovered and reused at least five times.

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“…Additionally, this strategy also reduces potential side reactions and improves selectivity. Recent studies have explored dehydrogenative strategies involving the reaction of 2-aminobenzyl alcohols with ketones or alcohols, employing various monometallic complexes built from elements such as Ni, Mn, Co, Ru, Rh, Ir, and Pd. − However, it is worth highlighting that there has been a relative lack of exploration into the synthesis of C-2-substituted quinolines starting directly from 2-nitrobenzyl alcohol using secondary alcohols. , …”

Section: Introductionmentioning

confidence: 99%

Dinuclear Ru(II) Schiff Base Complex Catalyzed One-Pot Synthesis of Quinolines through Acceptorless Dehydrogenative Coupling of Secondary Alcohols with 2-Nitrobenzyl Alcohol

Deshmukh,

Gharpure,

Murugavel

2024

Organometallics

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D i n u c l e a r R u ( I I ) c o m p l e x e s [ ( pcymene) 2 (RuCl) 2 L 1 ]2X (X = BF 4 (Ru1); X = PF 6 (Ru2)) and mononuclear [(p-cymene)have been synthesized and characterized by spectroscopic and analytical techniques. Dinuclear Ru1 and Ru2 orchestrate direct transformation of 2-nitrobenzyl alcohols to quinolines under mild conditions with significant efficiency even when employed at a minimal catalyst loading of 0.1 mol %. Proportional experiments carried out with the corresponding mononuclear complex Ru3 by keeping the Ru content the same (0.2 mol % of Ru3) reveal superior activity by the bimetallic system Ru1 for the one-pot quinoline synthesis. Late-stage functionalization of bioactive steroids and scaleup synthesis demonstrate the practical applicability of the present catalyst system. A probable mechanism of this conversion is proposed based on trapping of many of the intermediates by ESI-mass spectroscopy. These mechanistic studies have further been substantiated by ReactIR studies by monitoring the progress of the reaction in real time.

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Iron-catalysed quinoline synthesis via acceptorless dehydrogenative coupling

Abstract: An atom-economic and straightforward methodology for the synthesis of quinolines from α-2-aminoaryl alcohols and secondary alcohols is presented. Using earth-abundant and air-stable iron catalyst under activating agents (such as NaBHEt3),...

Cited by 19 publications

References 73 publications

Benzoquinone Ligand-Enabled Ruthenium-Catalyzed Deaminative Coupling of 2-Aminoaryl Aldehydes and Ketones with Branched Amines for Regioselective Synthesis of Quinoline Derivatives

Benzoquinone Ligand-Enabled Ruthenium-Catalyzed Deaminative Coupling of 2-Aminoaryl Aldehydes and Ketones with Branched Amines for Regioselective Synthesis of Quinoline Derivatives

Recyclable Ni-Containing Coordination Polymer as an Efficient Catalyst for the Synthesis of Oxindole and Quinoline Derivatives through the Borrowing Hydrogen Strategy

Dinuclear Ru(II) Schiff Base Complex Catalyzed One-Pot Synthesis of Quinolines through Acceptorless Dehydrogenative Coupling of Secondary Alcohols with 2-Nitrobenzyl Alcohol

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