Reduction of Aromatic Imino Derivatives: Chemical, Electrochemical, and Theoretical Studies

Port, Adriana; Sánchez-Aris, M; Cervelló, Enric; Jaime, Carlos; Virgili, Albert; Farriol, Maria; Gallardo, Iluminada

doi:10.1080/714040939

Cited by 4 publications

(3 citation statements)

References 11 publications

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“…In the presence of a strong reducing agent, like lithium aluminum hydride (LiAlH 4 ), with stronger and extreme reaction conditions, reduction of the imine group occurred, after reduction of the central ring. It was observed that in all cases, the aromatic ring was first reduced and only then imine group reduced, to the respective amines, with an exception of an anthracene derivative [133,183,184] . Adriana Port and co‐workers proposed two mechanisms for hydrogenation of imines in protic solvents – EEC (Electrochemical‐Electrochemical‐Chemical) and ECE (Electrochemical‐Chemical‐Electrochemical) methods.…”

Section: Electrochemical Hydrogenation Reactions (Ech)mentioning

confidence: 99%

“…It was observed that in all cases, the aromatic ring was first reduced and only then imine group reduced, to the respective amines, with an exception of an anthracene derivative. [133,183,184] Adriana Port and co-workers proposed two mechanisms for hydrogenation of imines in protic solvents -EEC (Electrochemical-Electrochemical-Chemical) and ECE (Electrochemical-Chemical-Electrochemical) methods. The former takes place in solvents with low proton donor capability whereas the latter in good proton donor capabilities.…”

Section: Electrochemical Hydrogenation Of Iminesmentioning

confidence: 99%

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Electrochemical Hydrogenation of Organic Compounds: A Sustainable Approach

Jayan,

Thadathil,

Varghese

2023

Asian J Org Chem

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Conventional methods for hydrogenation of organic compounds generally use corrosive catalysts and reagents, along with extreme conditions like high temperatures and pressures. Quenching of corrosive materials does not deter its negative impact on the environment, nor is one safe when it comes to working with high temperature and pressure. Electrochemical hydrogenation has proven to be safe and green since most of the efficient reactions are conducted at ambient pressure and temperature, without or minimizing the use of toxic catalysts and corrosive reagents as compared to conventional methods. This review therefore presents the advances in electrochemical hydrogenation reactions of organic compounds, starting from simple aliphatic compounds to complex polyaromatics and heterocyclic aromatic compounds.

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Section: Electrochemical Hydrogenation Reactions (Ech)mentioning

confidence: 99%

Section: Electrochemical Hydrogenation Of Iminesmentioning

confidence: 99%

Electrochemical Hydrogenation of Organic Compounds: A Sustainable Approach

Jayan,

Thadathil,

Varghese

2023

Asian J Org Chem

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“…10,11 The formed radical anion in the first step is rapidly protonated, resulting into a radical that will be easily reduced and finally protonated. Although the literature reveals the synthesis of amines using conventional methods, yet voltammetric methods are far better than the existing methods in the field with regards to their extra ordinary detection sensitivity, oligo determination capability, minimum detection limits, low cost, rapidity, accuracy, simplicity and non-destructive nature which have not been used for the said purpose.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of (1-ethyl-2-phenyl-1,4-dihydroquinolin-4-yl)-(2,4,6-trimethylphenyl)-amine by Electrochemical Methods in Aprotic Media

Kumari¹,

Sharma²

2011

Croat. Chem. Acta

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Abstract. The formation of (1-ethyl-2-phenyl-1,4-dihydroquinolin-4-yl)-(2,4,6-trimethylphenyl)-amine by the electro reduction of (1-ethyl-2-phenyl-1H-quinolin-4-ylidene)-(2,4,6-trimethylphenyl)-amine occurs through acceptance of two electrons accompanied by two successive peaks, each electron peak followed by a chemical reaction. The electrochemical reduction of (1-ethyl-2-phenyl-1H-quinolin-4-ylidene)-(2,4,6-trimethyl-phenyl)-amine was investigated in 0.1 M tetrabutylammoniumbromide in N,N-dimethylformamide at glassy carbon electrode using the technique of cyclic voltammetry at the room temperature (290K). In this medium the first peak was observed at -0.831 V (vs. Ag | Ag + ) at the glassy carbon electrode (GCE) surface, which is more stable and well defined as compared to the second peak. The diffusion coefficient (D) of investigated imine in the investigated solvent media has been calculated using the modified Randles-Sevcik equation. The electron transfer coefficient (α) of the reactant species has also been calculated. (doi: 10.5562/cca1855)

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Synthesis, characterization and preliminary investigation of the electro redox properties of anthracenyl-functionalized terpyridyl ligands

Adeloye

Ajibade

2011

Tetrahedron Letters

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Reduction of Aromatic Imino Derivatives: Chemical, Electrochemical, and Theoretical Studies

Cited by 4 publications

References 11 publications

Electrochemical Hydrogenation of Organic Compounds: A Sustainable Approach

Electrochemical Hydrogenation of Organic Compounds: A Sustainable Approach

Synthesis of (1-ethyl-2-phenyl-1,4-dihydroquinolin-4-yl)-(2,4,6-trimethylphenyl)-amine by Electrochemical Methods in Aprotic Media

Synthesis, characterization and preliminary investigation of the electro redox properties of anthracenyl-functionalized terpyridyl ligands

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