Electrocatalytic reduction of quinoline and its oxy derivatives

Kulakova, E. V.; Ivanova, N. M.; Kirilyus, I. V.; Makasheva, G. K.

doi:10.1134/s1023193511100107

Cited by 3 publications

(2 citation statements)

References 5 publications

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“…The electrocatalytic hydrogenation (ECH) of quinolone and its derivatives have been carried out in an electrolytic cell with an application of skeleton Ni catalyst for cathode activation that allows obtaining 1,2,3,4‐tetrahydroquinolines under mild conditions with high selectivity [93].…”

Section: The Strategies For Hydrogenationmentioning

confidence: 99%

Advances in the reduction of quinolines to 1,2,3,4‐tetrahydroquinolines

El‐Shahat

2021

Journal of Heterocyclic Chem

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The pursuit of modern sustainable chemistry has stimulated the development of innovative catalytic processes that enable chemical transformations to be performed under mild and clean conditions with high efficiency. Herein, we report that the hydrogenation of heteroaromatic compounds is one of the most efficient methods for the construction of heterocyclic skeletons, and only a few promising progress has been achieved. Transition metal‐catalyzed, a countless number of transition metals include have been used toward the development of homo/heterogeneous hydrogenation of quinolines via the most convenient route (Direct Hydrogenation) to obtain the corresponding tetrahydroquinoline derivatives.

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Section: The Strategies For Hydrogenationmentioning

confidence: 99%

Advances in the reduction of quinolines to 1,2,3,4‐tetrahydroquinolines

El‐Shahat

2021

Journal of Heterocyclic Chem

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“…However, such a strategy remains a yet unresolved goal on account of the challenge in merging the reduction of two reducible reactants and the coupling process into an ordered sequence. It is noteworthy that because of the high tunability of the potential, current, electrode, and electrolyte of electrochemistry, electroreduction has emerged as an appealing tool to create various chemical bonds. − As such, we anticipated that the electroreduction would offer a solution for the above synthetic purpose (Scheme c) by addressing the following issues: (1) selective reduction of two reducible reactants is required to avoids the generation of undesired cyclic amine and alcohol byproducts; (2) the radicals arising from carbonyls are stable enough to trap the N -heteroarenes; and (3) protonation is a key step to incorporate an H atom into the products because it is essential to suppress the thermodynamically favorable hydrogen evolution reaction (Δ G HER = −20 to −60 kcal/mol) on the cathode…”

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confidence: 99%

Room Temperature Construction of Vicinal Amino Alcohols via Electroreductive Cross-Coupling of N-Heteroarenes and Carbonyls

Wang

Zhang

et al. 2023

J. Am. Chem. Soc.

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Despite the widespread applications of α-hydroxyalkyl cyclic amines, direct and diverse access to such a class of unique vicinal amino alcohols still remains, to date, a challenge. Here, through a strategy of electroreductive α-hydroxyalkylation of inactive N-heteroarenes with ketones or electron-rich arylaldehydes, we describe a room temperature approach for the direct construction of α-hydroxyalkyl cyclic amines, which features a broad substrate scope, operational simplicity, high chemoselectivity, and no need for pressurized H 2 gas and transition metal catalysts. The zinc ion generated from anode oxidation plays a crucial role in the activation of both reactants by decreasing their reduction potentials. The strategy of electroreduction in combination with substrate activation by Lewis acids in this work is anticipated to develop more useful transformations.

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Electrochemical Hydrogenation of N‐Heterocycles and Related Substrates: A Mini‐Review

Garcia‐Torres,

Herbert

2024

Electrochemical Science Adv

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Catalytic hydrogenation refers to the (often) metal‐mediated addition of dihydrogen (H2) equivalents to unsaturated compounds to form new element‐hydrogen bonds. This conceptually simple reaction is ubiquitous in the production of a vast number of essential chemicals. Despite a growing recognition of the importance of sustainability in manufacturing, the use of fossil‐derived hydrogen gas and precious metal catalysts in hydrogenation remains widespread. Electrochemical variants of these processes are an appealing alternative, especially those that can make use of sustainable Brønsted acids, more abundant electrode materials and renewable electricity. In this mini‐review, we give a selective overview of electrochemical hydrogenation methodologies for N‐heterocycles and some related substrates from the specific perspective of the synthetic chemistry made possible by this increasingly popular approach.

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Electrocatalytic reduction of quinoline and its oxy derivatives

Cited by 3 publications

References 5 publications

Advances in the reduction of quinolines to 1,2,3,4‐tetrahydroquinolines

Advances in the reduction of quinolines to 1,2,3,4‐tetrahydroquinolines

Room Temperature Construction of Vicinal Amino Alcohols via Electroreductive Cross-Coupling of N-Heteroarenes and Carbonyls

Electrochemical Hydrogenation of N‐Heterocycles and Related Substrates: A Mini‐Review

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