Imines, enamines and oximes

Adams, Joseph P.

doi:10.1039/co9970400517

Cited by 26 publications

(10 citation statements)

References 311 publications

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“…In organic chemistry, it is well-documented that oximes are ambidentate nucleophiles, and their reactions with electrophilic reagents, e.g., alkylation, arylation, or acylation , have been extensively studied and reviewed. − Similar processes involving metal complexes are also known although scarce. , Metal-mediated iminoacylation of oximes is even a less explored area, and only recently have publications on this subject started to emerge in the literature.…”

Section: Metal-mediated Nitrile−oxime Couplingmentioning

confidence: 99%

Additions to Metal-Activated Organonitriles

Kukushkin

Pombeiro²

2002

Chem. Rev.

716

390

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Section: Metal-mediated Nitrile−oxime Couplingmentioning

confidence: 99%

Additions to Metal-Activated Organonitriles

Kukushkin

Pombeiro²

2002

Chem. Rev.

716

390

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“…In the case of imines, which are well-known for being important intermediates in the synthesis of biologically active heterocyclic compounds, α-amino acids, and α-amino alcohols, 27,28 great research efforts have been dedicated to finding different environmentally friendly alternatives to achieve the selective synthesis of imines. 29−31 Recently, several studies based on transition-metal-mediated catalytic routes have been developed.…”

Section: Introductionmentioning

confidence: 99%

Efficient Rare-Earth-Based Coordination Polymers as Green Photocatalysts for the Synthesis of Imines at Room Temperature

et al. 2018

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Five new rare-earth coordination polymers (CPs) were designed in order to offer a remarkable platform that contains light-harvesting antennas and catalytic active centers to achieve solar-energy conversion as green alternatives in the synthesis of imines. These five new spirobifluorene-containing Ln-CPs, named [Er(Hsfdc)(sfdc)(HO)]· xHO (RPF-30-Er), [Ln(Hsfdc)(sfdc)(EtOH)]·S (RPF-31-Ln, where Ln = La, Nd, and Sm and S = HO or EtOH), and [Ho(Hsfdc)(sfdc)(HO)] (RPF-32-Ho) (RPF = rare-earth polymeric framework and Hsfdc = 9,9'-spirobi[9 H-fluorene]-2,2'-dicarboxylic acid), have been solvothermally synthesized, and their structural features can be described as follows: (i) RPF-30-Er shows a 3D framework in which the inorganic trimers (secondary building units) are cross-linked by Hsfdc and sfdc linkers displaying a pcu topology. (ii) The isostructural RPF-31-Ln series of materials, together with RPF-32-Ho, exhibit a 1D network of chains growing along the a axis with a ribbon-of-rings topology type. The photocatalytic activity of the RPF- n materials was tested in the oxidative coupling of amines using molecular oxygen and air as oxidizing agents under warm light. Among the materials investigated, RPF-31-Nd was chosen to further investigate the approach in the selectivity of different amine derivates.

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“…Imines and their derivatives are versatile synthetic intermediates that have been extensively utilized for synthesis of dyes, fragrances, fungicides, pharmaceuticals, and agricultural chemicals . In general, there are presently three commonly utilized approaches for imines synthesis, that is, condensation of amines with ketones or aldehydes (Figure , path A), oxidative self‐coupling of amines (path B), and oxidative coupling of amines with alcohols (path C) .…”

Section: Introductionmentioning

confidence: 99%

Selective hydrogenation of nitriles to imines over a multifunctional heterogeneous Pt catalyst

Long

Yin

et al. 2014

AIChE Journal

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in Wiley Online Library (wileyonlinelibrary.com)Imines and their derivatives are versatile synthetic intermediates for the industrial preparation of both bulk and fine chemicals and for pharmaceuticals, but preparing these compounds efficiently through direct hydrogenation of nitriles are hindered by overhydrogenation to secondary amines. Here we report a highly efficient multifunctional catalyst system for selective hydrogenation coupling of nitriles to secondary imines using a heterogeneous Pt catalyst that was deposited on a nickel-based metal-organic framework (MOF) containing DABCO. The catalyst showed excellent synergy in promoting the hydrogenation of a variety of nitriles, giving significantly improved activity and selectivity (up to >99% yield) even under atmospheric pressure of H 2 . It is suggested that the Lewis base (DABCO) sites on the Ni-MOF inhibit further hydrogenation of the imines. The influence of H 2 pressure, reactant concentration, stirring speed, and reaction temperature was investigated. The kinetics and mechanism of hydrogenation of benzonitrile (BN) by the Pt/Ni-MOF catalyst has been studied. The reaction showed a first-order dependence on both BN concentration and H 2 pressure. A kinetic model was proposed based on the mechanism of nitriles hydrogenation and compared with experimental observations.

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Imines, enamines and oximes

Cited by 26 publications

References 311 publications

Additions to Metal-Activated Organonitriles

Additions to Metal-Activated Organonitriles

Efficient Rare-Earth-Based Coordination Polymers as Green Photocatalysts for the Synthesis of Imines at Room Temperature

Selective hydrogenation of nitriles to imines over a multifunctional heterogeneous Pt catalyst

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