A multigram-scale lower E-factor procedure for MIBA-catalyzed direct amidation and its application to the coupling of alpha and beta aminoacids

Fatemi, S. Jamil. A.; Gernigon, Nicolas; Hall, Dennis G.

doi:10.1039/c5gc00659g

Cited by 56 publications

(24 citation statements)

References 24 publications

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“…kg waste/kg product). [46] This method provided synthesis of a variety of dipeptides with protected α-amino acid precursors and tetrapeptides with β-amino acids. While the yields for reactions featuring sterically hindered monomers were only moderate, the green nature of the reaction conditions, as well the requirement for only mild heating (40 C) are a platform to build on.…”

Section: Alternative Approaches To Noncanonical Amidationmentioning

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: Alternative Approaches To Noncanonical Amidationmentioning

confidence: 99%

Recent developments in catalytic amide bond formation

Todorovic

Perrin

2020

Peptide Science

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“…In particular, arguably the biggest drive to investigate these methods came from the success of solid-phase peptide synthesis (SPPS) [11]. Nevertheless, most of them require an active form of carboxylic acid (formed either in a separate synthetic step or in situ, for example, in a reaction with a so-called "coupling reagent"), which is subsequently attacked by a nucleophile in the next step [12,13]. Moreover, common coupling reagents (e.g., carbodiimides, phosphonium, or uronium salts [14][15][16]) are often rather expensive, toxic, and are used in stoichiometric quantities…”

Section: Introductionmentioning

confidence: 99%

Microwave-Assisted Catalytic Method for a Green Synthesis of Amides Directly from Amines and Carboxylic Acids

2020

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Amide bonds are among the most interesting and abundant molecules of life and products of the chemical pharmaceutical industry. In this work, we describe a method of the direct synthesis of amides from carboxylic acids and amines under solvent-free conditions using minute quantities of ceric ammonium nitrate (CAN) as a catalyst. The reactions are carried out in an open microwave reactor and allow the corresponding amides to be obtained in a fast and effective manner when compared to other procedures of the direct synthesis of amides from acids and amines reported so far in the literature. The amide product isolation procedure is simple, environmentally friendly, and is performed with no need for chromatographic purification of secondary amides due to high yields. In this report, primary amines were used in most examples. However, the developed procedure seems to be applicable for secondary amines as well. The methodology produces a limited amount of wastes, and a catalyst can be easily separated. This highly efficient, robust, rapid, solvent-free, and additional reagent-free method provides a major advancement in the development of an ideal green protocol for amide bond formation.

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“…These reactions can be scaled up to access multigram quantities of amide with very high efficiency (PMI from [5][6][7][8][9][10][11][12][13]. The most commonly reported amidation catalysts are boronic acids, ranging from simple examples (phenyl, n-butyl), to more complex functionalised systems 11,[25][26][27][28][29] . Each system has been reported to offer particular advantages, from lower temperature reactions, to wider substrate tolerance or increased reaction rate.…”

Section: Boron-based Catalysts Boron Compounds Constitute the Other mentioning

confidence: 99%

A green chemistry perspective on catalytic amide bond formation

et al. 2019

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The synthesis of amides is of widespread importance, and there has been considerable recent interest in the development of catalytic methods to access these molecules. In this perspective article, we provide an overview of the current state-of-the-art of amide synthesis, and assess new catalytic amide formation methods in the context of efficiency and sustainability. The advantages and disadvantages of catalytic approaches are highlighted and areas for future research are identified.

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A multigram-scale lower E-factor procedure for MIBA-catalyzed direct amidation and its application to the coupling of alpha and beta aminoacids

Abstract: More economical conditions for direct amidation between amines and carboxylic acids, including α- and β-amino acids, have been optimized using the MIBA catalyst (5-methoxy-2-iodophenylboronic acid, 6).

Cited by 56 publications

References 24 publications

Recent developments in catalytic amide bond formation

Recent developments in catalytic amide bond formation

Microwave-Assisted Catalytic Method for a Green Synthesis of Amides Directly from Amines and Carboxylic Acids

A green chemistry perspective on catalytic amide bond formation

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