Zirconium-catalyzed direct amide bond formation between carboxylic esters and amines

Lenstra, Danny C.; Nguyen, D. Thao; Mecinović, Jasmin

doi:10.1016/j.tet.2015.06.066

Cited by 36 publications

(20 citation statements)

References 35 publications

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“…Zirconium salts, for example, ZrCl 4 [123] and ZrCp 2 Cl 2, [124] have also been identified as competent catalysts for the amidation of methyl esters (Table 2). Both systems have been demonstrated in contexts relevant to peptide chemistry, amidating amino acid methyl esters, including pyroglumate precursors for the ultimate synthesis of ATPgated ion channel antagonists.…”

Section: Other Ester Amidation Methodsmentioning

confidence: 99%

Recent developments in catalytic amide bond formation

Todorovic

Perrin

2020

Peptide Science

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Amide bond forming reactions are critical for both polypeptide synthesis and medicinal chemistry. Most current approaches for amidation employ stoichiometric activating agents, but such methods are neither atom economical nor synthetically elegant. Catalytic approaches for amidation are potentially green and more ideal substitutes for current standard methods and thus are the subject of this review. Such methods face significant thermodynamic and kinetic barriers and have, as a result, historically

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Section: Other Ester Amidation Methodsmentioning

confidence: 99%

Recent developments in catalytic amide bond formation

Todorovic

Perrin

2020

Peptide Science

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“…Most of them require heating to above 100 °C such as A large number of metallic compounds have been proposed as catalysts for the direct amidification of carboxylic acids with amines. Most of them require heating to above 100 • C such as (cyclopentadienyl) 2 ZrCl 2 [173] and Nb 2 O 5 [174]. The combination of Ph 3 P + CCl 4 has been found to catalyze direct amidifications [175].…”

Section: Direct Amide Bond Formation From Amines and Carboxylic Acidsmentioning

confidence: 99%

Organocatalysis: Fundamentals and Comparisons to Metal and Enzyme Catalysis

et al. 2016

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Catalysis fulfills the promise that high-yielding chemical transformations will require little energy and produce no toxic waste. This message is carried by the study of the evolution of molecular catalysis of some of the most important reactions in organic chemistry. After reviewing the conceptual underpinnings of catalysis, we discuss the applications of different catalysts according to the mechanism of the reactions that they catalyze, including acyl group transfers, nucleophilic additions and substitutions, and C-C bond forming reactions that employ umpolung by nucleophilic additions to C=O and C=C double bonds. We highlight the utility of a broad range of organocatalysts other than compounds based on proline, the cinchona alkaloids and binaphthyls, which have been abundantly reviewed elsewhere. The focus is on organocatalysts, although a few examples employing metal complexes and enzymes are also included due to their significance. Classical Brønsted acids have evolved into electrophilic hands, the fingers of which are hydrogen donors (like enzymes) or other electrophilic moieties. Classical Lewis base catalysts have evolved into tridimensional, chiral nucleophiles that are N-(e.g., tertiary amines), P-(e.g., tertiary phosphines) and C-nucleophiles (e.g., N-heterocyclic carbenes). Many efficient organocatalysts bear electrophilic and nucleophilic moieties that interact simultaneously or not with both the electrophilic and nucleophilic reactants. A detailed understanding of the reaction mechanisms permits the design of better catalysts. Their construction represents a molecular science in itself, suggesting that sooner or later chemists will not only imitate Nature but be able to catalyze a much wider range of reactions with high chemo-, regio-, stereo-and enantioselectivity. Man-made organocatalysts are much smaller, cheaper and more stable than enzymes.

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“…An interesting approach to functionalize GO is through amide or ester bond between the oxygenated groups, for example, on the carboxylate groups using activating coupling reagents such as thionyl chloride (SOCl 2 ), 1‐ethyl‐3‐(3‐dimethylaminopropyl) carbodiimide (EDC), and N , N ′‐dicyclohexylcarbodiimide (DCC) . Specifically, linkage by an amide bond by using modifiers with terminal amine groups (R‐NH 2 ) is interesting due to its high stability, not susceptible easily to hydrolysis, thus has been greatly pursued for obtaining novel graphene‐functionalized materials …”

Section: Introductionmentioning

confidence: 99%

Covalently linked nanocomposites of polypyrrole with graphene: Strategic design toward optimized properties

Naidek

Zarbin

Orth

2018

J. Polym. Sci. Part A: Polym. Chem.

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Graphene-based nanocomposites with conducting polymers have attracted increasing interest due to the enhanced synergistic properties, which can potentiate and broaden applications. In this context, covalent functionalization stands out as a strategic designing tool, which optimizes the interaction between the nanocomposites components. Herein, covalently linked polymeric nanocomposites were obtained between graphene derivatives and polypyrrole (Ppy) under mild routes (i.e., aqueous, room temperature). First, pyrrole was covalently functionalized on graphene oxide (GO) through stable amide bonds and further polymerization with FeCl 3 led to the polymeric nanocomposites. Finally, to improve conductivity, GO was reduced using NaBH 4 . Similarly, analogous noncovalent nanocomposites were obtained for comparison purposes. All samples were thoroughly characterized by thermogravimetric analysis, scanning electron microscopy, and infrared and Raman spectroscopy, confirming the targeted functionalization, polymerization, and reduction processes. Moreover, the covalent link effectively enhances the interaction of the nanocomposite's components as evidenced by its improved electrochemical stability (300 cycles), compared to the non-covalent composites which loses conductivity in the initial stages. Indeed, Ppy is known for its low stability, limiting its applications. Overall, the results herein evidence that covalently linked nanocomposites can be successfully obtained with optimized electrochemical response, promising for applications as supercapacitors and artificial muscles.

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Zirconium-catalyzed direct amide bond formation between carboxylic esters and amines

Cited by 36 publications

References 35 publications

Recent developments in catalytic amide bond formation

Recent developments in catalytic amide bond formation

Organocatalysis: Fundamentals and Comparisons to Metal and Enzyme Catalysis

Covalently linked nanocomposites of polypyrrole with graphene: Strategic design toward optimized properties

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