Transamidation of primary carboxamides, phthalimide, urea and thiourea with amines using Fe(OH)3@Fe3O4 magnetic nanoparticles as an efficient recyclable catalyst

Arefi, Marzban; Heydari, Akbar

doi:10.1039/c5ra27680b

Cited by 29 publications

(14 citation statements)

References 39 publications

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“…Al arge number of approaches have been developed for the transamidation reactionofp rimarya mides, under both stoichiometric and catalytic conditions. [83][84][85][86][87][88][89][90][91][92] However,t he transamidation of secondary or tertiarya mides has been less well-explored,o wing to the high stabilityo ft he amide bond, which is causedb yr esonance effects and unfavorable thermodynamics or thermoneutrality. [93,94] However,afew reports have managed to overcome the challenges associated with the transamidation of secondary amides.…”

Section: Transamidation Reactionsmentioning

confidence: 99%

“…The transamidation reaction is one of the most‐studied transformations in organic synthesis, owing to the ubiquity of the amide functional group in bioactive molecules. A large number of approaches have been developed for the transamidation reaction of primary amides, under both stoichiometric and catalytic conditions . However, the transamidation of secondary or tertiary amides has been less well‐explored, owing to the high stability of the amide bond, which is caused by resonance effects and unfavorable thermodynamics or thermoneutrality .…”

Section: Reactions Of Amides Through N−c Activationmentioning

confidence: 99%

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Recent Advances in the Metal‐Catalyzed Activation of Amide Bonds

Chaudhari

Gnanaprakasam

2018

Chemistry An Asian Journal

128

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The amide functional group is commonly found in peptides, proteins, pharmaceutical compounds, natural products, andp olymers.T he synthesis of amides is typically performed by using classical approaches that involvet he reaction between ac arboxylic acid and an amine in the presence of an activator.Amides are thought to be an inert functional group, because they are unsusceptible to nucleophile attack, owing to their low electrophilicity.T he reason fort his resistancei sc lear:t he resonance stability of the amide bond. However,t ransition metal catalysis can circumvent this stability by selectively rupturing the NÀCb ond of the amide, thereby facilitating further cross-couplingo ro ther reactions.Inthis Focus Review,wediscuss the recent advances in this area and present as ummary of methods that have been developed for activating the amide NÀCb ond by using precious and non-preciousmetals.

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Section: Transamidation Reactionsmentioning

confidence: 99%

Section: Reactions Of Amides Through N−c Activationmentioning

confidence: 99%

Recent Advances in the Metal‐Catalyzed Activation of Amide Bonds

Chaudhari

Gnanaprakasam

2018

Chemistry An Asian Journal

128

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“…It is also simple to prepare, and the reaction can be performed with DMF as an example of a tertiary amide. On the other hand, the method described by Heidari and Arefi [ 28 ] has a better substrate scope and uses smaller quantities of catalyst. Unfortunately, the preparation process for the catalyst is more complicated and uses simple iron salts as precursors; this is potentially problematic since the authors did not quantify the free salts in their catalyst, and it is possible that some remaining salts are responsible for the transformation, on the other hand if the simple salts are good and suitable catalysts for this reactions, prepare a catalysts that do not provide very different results using them a starting materials consumes time unnecessarily.…”

Section: Metal-catalyzed Direct Transamidationsmentioning

confidence: 99%

Direct Transamidation Reactions: Mechanism and Recent Advances

2018

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Amides are undeniably some of the most important compounds in Nature and the chemical industry, being present in biomolecules, materials, pharmaceuticals and many other substances. Unfortunately, the traditional synthesis of amides suffers from some important drawbacks, principally the use of stoichiometric activators or the need to use highly reactive carboxylic acid derivatives. In recent years, the transamidation reaction has emerged as a valuable alternative to prepare amides. The reactivity of amides makes their direct reaction with nitrogen nucleophiles difficult; thus, the direct transamidation reaction needs a catalyst in order to activate the amide moiety and to promote the completion of the reaction because equilibrium is established. In this review, we present research on direct transamidation reactions ranging from studies of the mechanism to the recent developments of more applicable and versatile methodologies, emphasizing those reactions involving activation with metal catalysts.

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“…In continuation of our previous work on transamidation, herein, for the first time we report the magnetic nanoparticle supported by guanidine acetic acid (MNPs‐GAA) as a novel, eco‐friendly, and reusable catalyst for transamidation of carboxamides with amines under solvent free conditions (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Guanidine Acetic Acid Functionalized Magnetic Nanoparticles: Recoverable Green Catalyst for Transamidation

et al. 2016

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In the presence of a catalytic amount of Fe3O4‐Guanidine acetic acid (GAA) nanoparticles, efficient transamidation of several amides with various amines is described under solvent‐free conditions. Fe3O4‐Guanidine acetic acid nanoparticles provide the first example of a magnetically recoverable organocatalyst for transamidation in the highest catalytic activity. The catalyst could be simply recycled with the assistance of an external magnet and reused for six runs without significant loss of its catalytic activity.

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Transamidation of primary carboxamides, phthalimide, urea and thiourea with amines using Fe(OH)₃@Fe₃O₄ magnetic nanoparticles as an efficient recyclable catalyst

Abstract: The highly efficient transamidation of primary amides, phthalimide, urea and thiourea with amines catalyzed by magnetic Fe3O4@Fe(OH)3 nanoparticles is described.

Cited by 29 publications

References 39 publications

Recent Advances in the Metal‐Catalyzed Activation of Amide Bonds

Recent Advances in the Metal‐Catalyzed Activation of Amide Bonds

Direct Transamidation Reactions: Mechanism and Recent Advances

Guanidine Acetic Acid Functionalized Magnetic Nanoparticles: Recoverable Green Catalyst for Transamidation

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