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Catalysts
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Catalytic Approaches for Amide Synthesis
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Catalytic Approaches for Amide Synthesis

A special issue of Catalysts (ISSN 2073-4344). This special issue belongs to the section "Catalysis in Organic and Polymer Chemistry".

Deadline for manuscript submissions: closed (20 October 2021) | Viewed by 11165

Special Issue Editors

Dr. Marcia De Figueiredo

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Guest Editor
Institut Charles Gerhardt – UMR 5253 CNRS, Ecole Nationale Supérieur de Chimie de Montpellier, Montpellier cedex 5, France
Interests: organocatalysis; catalytic asymmetric methodologies; total synthesis of natural products and biologically active targets as well as amide synthesis
Dr. Jean‐Marc Campagne

E-Mail Website
Guest Editor
Institut Charles Gerhardt – UMR 5253 CNRS, Ecole Nationale Supérieur de Chimie de Montpellier, CEDEX 5, Montpellier, France
Interests: homogeneous catalysis; metal- and organocatalysis; organic synthesis; enantioselective synthesis; development of new synthetic methods; natural products

Special Issue Information

Dear Colleagues,

Amides are essential structural motifs in peptides, pharmaceuticals, and natural/synthetic polymers. Therefore, the amide bond formation is one of the most performed reaction in both academic and industrial fields. Traditionally amides have been obtained from carboxylic acids and amines in the presence of a stoichiometric amount of a complex peptide coupling reagent. These reactions are usually not catalytic, the atom economy is dramatically low, and large quantities of non-valorized by-products are formed.

To enable amide bond formation under milder/greener conditions, catalysis in its broader sense offers alternative strategies allowing direct amidation between carboxylic acid and amines, but also expands the scope of coupling partners to amine and carboxylic acids surrogates.

This Special Issue welcomes both review and original research articles on all aspects of heterogeneous and homogeneous catalysis. Topics include, but are not limited to, the following:

  • Direct amidation
  • Organocatalyzed amidation
  • C-H bond amidation
  • TM catalyzed amidation
  • Transamidation
  • Photoredox catalyzed amidation
  • Oxidative amidation
  • Reductive amidation
  • Carbonylative amidation
  • Decarbonylative amidation
  • Amidation via rearrangements
  • Hydration strategies
  • ‘Carboxylic acid surrogates’ amidation
  • ‘Amine surrogates’ amidation

Prof. Dr. Jean‐Marc Campagne
Dr. Marcia De Figueiredo
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Catalysts is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2200 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Amidation
  • Organocatalysis
  • Photoredox
  • C-H functionalization
  • Azides
  • Isocyanide
  • Carboxylic acids
  • Amines
  • Carbonylation
  • Transamidation

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Published Papers (3 papers)

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Research

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12 pages, 3262 KiB  
Article
Amide-Type Substrates in the Synthesis of N-Protected 1-Aminomethylphosphonium Salts
by Dominika Kozicka, Paulina Zieleźny, Karol Erfurt and Jakub Adamek
Catalysts 2021, 11(5), 552; https://doi.org/10.3390/catal11050552 - 27 Apr 2021
Cited by 4 | Viewed by 2435
Abstract
Herein we describe the development and optimization of a two-step procedure for the synthesis of N-protected 1-aminomethylphosphonium salts from imides, amides, carbamates, or lactams. Our “step-by-step” methodology involves the transformation of amide-type substrates to the corresponding hydroxymethyl derivatives, followed by the substitution [...] Read more.
Herein we describe the development and optimization of a two-step procedure for the synthesis of N-protected 1-aminomethylphosphonium salts from imides, amides, carbamates, or lactams. Our “step-by-step” methodology involves the transformation of amide-type substrates to the corresponding hydroxymethyl derivatives, followed by the substitution of the hydroxyl group with a phosphonium moiety. The first step of the described synthesis was conducted based on well-known protocols for hydroxymethylation with formaldehyde or paraformaldehyde. In turn, the second (substitution) stage required optimization studies. In general, reactions of amide, carbamate, and lactam derivatives occurred at a temperature of 70 °C in a relatively short time (1 h). On the other hand, N-hydroxymethylimides reacted with triarylphosphonium salts at a much higher temperature (135 °C) and over longer reaction times (as much as 30 h). However, the proposed strategy is very efficient, especially when NaBr is used as a catalyst. Moreover, a simple work-up procedure involving only crystallization afforded good to excellent yields (up to 99%). Full article
(This article belongs to the Special Issue Catalytic Approaches for Amide Synthesis)
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11 pages, 2618 KiB  
Article
Direct Amide Synthesis over Composite Magnetic Catalysts in a Continuous Flow Reactor
by Yawen Liu and Evgeny V. Rebrov
Catalysts 2021, 11(2), 146; https://doi.org/10.3390/catal11020146 - 20 Jan 2021
Cited by 10 | Viewed by 2843
Abstract
Composite magnetic catalysts containing different amounts of sulfated titania (33–50 wt %) have been prepared by means of high energy ball-milling between TiO2 and NiFe2O4. The catalysts have been characterized with N2 adsorption/desorption isotherms, XRD, temperature programmed [...] Read more.
Composite magnetic catalysts containing different amounts of sulfated titania (33–50 wt %) have been prepared by means of high energy ball-milling between TiO2 and NiFe2O4. The catalysts have been characterized with N2 adsorption/desorption isotherms, XRD, temperature programmed oxidation (TPO) and vibrating sample magnetometer (VSM). The catalytic activity was measured in the reaction of aniline and 4-phenylbutyric acid in the continuous mode under conventional and inductive heating. The effect of catalyst loading in the reactor on reaction and deactivation has been studied, indicating the catalyst containing 50 wt % titania gave the highest reaction rate and least deactivation. The operation in a flow reactor under inductive heating increased the amide yield by 25% as compared to conventional heating. The initial reaction rate decreased by 30% after a period of 15 h on stream. The catalyst activity was fully restored after a treatment with an air flow at 400 °C. Full article
(This article belongs to the Special Issue Catalytic Approaches for Amide Synthesis)
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Review

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17 pages, 3576 KiB  
Review
Enantioselective Catalytic C-H Amidations: An Highlight
by Eleonora Tosi, Renata Marcia de Figueiredo and Jean-Marc Campagne
Catalysts 2021, 11(4), 471; https://doi.org/10.3390/catal11040471 - 6 Apr 2021
Cited by 14 | Viewed by 4051
Abstract
The crucial role played by compounds bearing amide functions, not only in biological processes but also in several fields of chemistry, life polymers and material sciences, has brought about many significant discoveries and innovative approaches for their chemical synthesis. Indeed, a plethora of [...] Read more.
The crucial role played by compounds bearing amide functions, not only in biological processes but also in several fields of chemistry, life polymers and material sciences, has brought about many significant discoveries and innovative approaches for their chemical synthesis. Indeed, a plethora of strategies has been developed to reach such moieties. Amides within chiral molecules are often associated with biological activity especially in life sciences and medicinal chemistry. In most of these cases, their synthesis requires extensive rethinking methodologies. In the very last years (2019–2020), enantioselective C-H functionalization has appeared as a straightforward alternative to reach chiral amides. Therein, an overview on these transformations within this timeframe is going to be given. Full article
(This article belongs to the Special Issue Catalytic Approaches for Amide Synthesis)
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