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Catalysts
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Metal-Catalyzed Processes in One-Pot Syntheses of Heterocycles
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Metal-Catalyzed Processes in One-Pot Syntheses of Heterocycles

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 (31 January 2023) | Viewed by 8311

Special Issue Editors

Prof. Dr. Thomas J. J. Müller

E-Mail Website
Guest Editor
Heinrich-Heine-University Düsseldorf Institute of Organic and Macromolecular Chemistry I 40225 Düsseldorf
Interests: functional chromophores, electrophores, and pharmacophores; heterocyclic chemistry; diversity-oriented synthesis; multicomponent reactions; sequential catalysis
Prof. Dr. Eelco Ruijter

E-Mail Website
Guest Editor
Department of Chemistry and Pharmaceutical Sciences and Amsterdam Institute for Molecules, Medicines & Systems (AIMMS), Vrije Universiteit Amsterdam, De Boelelaan 1108, 1081 HZ Amsterdam, The Netherlands
Interests: novel cascade reactions; transition metal catalysis; asymmetric synthesis; applications in the synthesis of pharmaceutically relevant heterocycles and natural product analogs

Special Issue Information

Dear Colleagues,

The advent of metal catalysis has provided a fascinating tool for significantly facilitating the synthesis of complex and functional molecules as well as natural products. In particular, the broad tolerance for many polar functional groups has set the stage for going beyond simple ligation by forming a single bond between two reactants. Therefore, metal catalysis has opened new avenues to one-pot processes, where all elementary steps proceed in the same reaction vessel. Among these one-pot reactions are multicomponent and domino reactions as well as metal-catalyzed cascade reactions. This Special Issue aims to offer a stage for sharing and discussing recent results from your laboratories on this fascinating synthetic strategy. Furthermore, it will stimulate the scientific community to further develop the concept.

We look forward to receiving your esteemed contributions to this Special Issue.

Prof. Dr. Thomas J. J. Müller
Prof. Dr. Eelco Ruijter
Guest Editors

Manuscript Submission Information

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Keywords

  • cascade reactions
  • consecutive sequences
  • domino reactions
  • multicomponent reactions
  • one-pot reactions
  • sequential catalysis

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Published Papers (3 papers)

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Research

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14 pages, 4246 KiB  
Article
Palladium-Catalyzed Domino Cycloisomerization/Double Condensation of Acetylenic Acids with Dinucleophiles
by Nerea Conde, María Teresa Herrero, Garazi Urgoitia and Raul SanMartin
Catalysts 2022, 12(2), 127; https://doi.org/10.3390/catal12020127 - 21 Jan 2022
Cited by 5 | Viewed by 3035
Abstract
Metal-catalyzed cascade processes based on hydrofunctionalization of alkynes are receiving much more attention because of their potential to provide advantageous approaches to otherwise synthetically challenging compounds. An alternative catalyst system has been found for the domino cycloisomerization/cyclocondensation reaction involving acetylenic acids and heterodinucleophiles. [...] Read more.
Metal-catalyzed cascade processes based on hydrofunctionalization of alkynes are receiving much more attention because of their potential to provide advantageous approaches to otherwise synthetically challenging compounds. An alternative catalyst system has been found for the domino cycloisomerization/cyclocondensation reaction involving acetylenic acids and heterodinucleophiles. A CNN pincer palladium(II) complex, acting as a homogeneous catalyst, provides the corresponding polyheterocycles with a higher substrate/catalyst ratio. Other palladium sources were also tested and discarded, and a number of mechanistic studies including poisoning assays, kinetic plots, TEM images, XRD spectra and UPLC-MS analysis of reaction intermediates were conducted in order to shed light on the role of this pincer catalyst and the catalytic cycle involved in the cascade reaction. As a result, a more nuanced mechanism is tentatively proposed. Full article
(This article belongs to the Special Issue Metal-Catalyzed Processes in One-Pot Syntheses of Heterocycles)
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Review

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21 pages, 10827 KiB  
Review
Ru-Catalyzed One-Pot Synthesis of Heterocyclic Backbones
by Vaezeh Fathi Vavsari, Mehri Seyed Hashtroudi and Saeed Balalaie
Catalysts 2023, 13(1), 87; https://doi.org/10.3390/catal13010087 - 1 Jan 2023
Cited by 2 | Viewed by 2207
Abstract
Ruthenium complexes are remarkable catalysts for the C–H activation approaches and organic transformations. Combining a Ru-catalyst with oxidants and other additives in a one-pot process is considered a sustainable approach due to the reduction in reaction steps and the minimal usage of solvents [...] Read more.
Ruthenium complexes are remarkable catalysts for the C–H activation approaches and organic transformations. Combining a Ru-catalyst with oxidants and other additives in a one-pot process is considered a sustainable approach due to the reduction in reaction steps and the minimal usage of solvents during synthesis, work-up, isolation of chemicals, and purification of the products. This review highlights the ruthenium-catalyzed organic transformations in a one-pot manner to achieve heterocyclic backbones, including indoles, benzofurans, indazoles, pyrans, pyrimidines, quinolines, and isoquinolines. Full article
(This article belongs to the Special Issue Metal-Catalyzed Processes in One-Pot Syntheses of Heterocycles)
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29 pages, 21117 KiB  
Review
Heterocycles by Consecutive Multicomponent Syntheses via Catalytically Generated Alkynoyl Intermediates
by Jonas Niedballa and Thomas J. J. Müller
Catalysts 2022, 12(1), 90; https://doi.org/10.3390/catal12010090 - 13 Jan 2022
Cited by 15 | Viewed by 2460
Abstract
Multicomponent processes are beneficial tools for the synthesis of heterocycles. As densely substituted bifunctional electrophiles, ynones are essential intermediates by applying cyclocondensations or cycloadditions in numerous heterocycle syntheses. The respective alkynoyl intermediates are generally accessible by palladium-, copper- and palladium/copper-catalyzed alkynylation. In turn, [...] Read more.
Multicomponent processes are beneficial tools for the synthesis of heterocycles. As densely substituted bifunctional electrophiles, ynones are essential intermediates by applying cyclocondensations or cycloadditions in numerous heterocycle syntheses. The respective alkynoyl intermediates are generally accessible by palladium-, copper- and palladium/copper-catalyzed alkynylation. In turn, the mild reaction conditions allow for a fast and versatile entry to functional heterocycles in the sense of consecutive multicomponent processes. This review collates and presents recent advances in accessing thirteen heterocycle classes and their applications by virtue of catalytic alkynoyl generation in diversity-oriented multicomponent syntheses in a one-pot fashion. Full article
(This article belongs to the Special Issue Metal-Catalyzed Processes in One-Pot Syntheses of Heterocycles)
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