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Green and Environmentally Friendly Visible-Light- and Transition Metal-Catalyzed Synthesis

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: 30 August 2025 | Viewed by 1858

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Faculty of Chemistry and Chemical Technology, University of Ljubljana, Ljubljana, Slovenia
Interests: organic synthesis; transition metal catalysis; photocatalysis; heterocyclic chemistry; organic days; surface modification
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Special Issue Information

Dear Colleagues,

Green or environmentally friendly synthesis methods (including visible light photocatalysis and reactions catalyzed by transition metals) are in high demand in the field of organic synthesis as they can reduce or eliminate the use or generation of hazardous substances, and thus promise a significant reduction in pollution and energy consumption. In addition, medicinal chemistry is a key area for the discovery and development of new and innovative drugs for the treatment or management of various diseases, some of which are life-threatening. Therefore, further contributions to the fields of medicinal chemistry and materials science are of fundamental importance for the well-being of mankind as a whole. At the same time, researchers in the field of synthetic chemistry need to focus their efforts on conducting research into environmentally friendly synthetic processes, as pollution has reached unacceptable levels in some parts of the world. Therefore, synthetic strategies need to be developed that synergistically combine activities in these two important areas in order to effectively control pollution exposure and energy consumption at the same time. The aim of this Special Issue is to highlight the research endeavors that are being carried out to solve the above problems. Scientists and researchers in this field are invited to contribute to this Special Issue.

Prof. Dr. Bogdan Štefane
Guest Editor

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Keywords

  • green synthesis
  • sustainable chemistry
  • transition metal catalysis
  • light induced transformations
  • photoredox catalysis
  • organic synthesis

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Published Papers (2 papers)

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Research

28 pages, 775 KiB  
Article
Towards Greener Synthesis of Substituted 3-Aminophthalates Starting from 2H-Pyran-2-ones via Diels–Alder Reaction of Acetylenedicarboxylates
by Dominik Fendre, Miha Lukšič and Krištof Kranjc
Molecules 2025, 30(11), 2271; https://doi.org/10.3390/molecules30112271 - 22 May 2025
Abstract
The aim of this work was to prepare a large set of variously substituted 3-aminophthalates starting from substituted 3-acylamino-2H-pyran-2-ones acting as dienes in Diels–Alder reactions with dialkyl acetylenedicarboxylates having the role of dienophiles. These thermally allowed [4+2] cycloadditions were taking place [...] Read more.
The aim of this work was to prepare a large set of variously substituted 3-aminophthalates starting from substituted 3-acylamino-2H-pyran-2-ones acting as dienes in Diels–Alder reactions with dialkyl acetylenedicarboxylates having the role of dienophiles. These thermally allowed [4+2] cycloadditions were taking place with normal electron demand due to rather electron-deficient dienophiles and relatively electron-rich dienes; however, they still required quite harsh reaction conditions: heating in closed vessels at 190 °C for up to 17 h was sufficient in most cases (albeit for a few reactions the time needed was up to 58 h) to achieve conversions above 95%. Such conditions, unfortunately, necessitated the use of a larger excess of dienophiles (as undesired polymerization takes place concomitantly); nevertheless, the straightforward isolation procedures enabled access to the target compounds in moderate to high yields (average yield 56%). All products were characterized by standard analytical and spectroscopic methods. With the goal of changing the reaction conditions to be more environmentally friendly, we investigated the effect of various solvents (water, n-butanol, butyl acetate, xylene, para-cymene, n-nonane, etc.) and the temperature applied (130–190 °C) on the conversion. We found that higher temperatures are necessary in most cases (except for the most reactive 2H-pyran-2-ones) regardless of the solvent used. Relative reactivity was determined for both sets of reactants and the experimentally obtained data show good agreement with the computational results. Full article
15 pages, 2526 KiB  
Article
Iridium-Catalyzed Highly Selective 1,4-Reduction of α,β-Unsaturated Carbonyl Compounds
by Youwei Chen, Jide Li, Jiaxi Xu and Zhanhui Yang
Molecules 2024, 29(24), 5912; https://doi.org/10.3390/molecules29245912 - 14 Dec 2024
Viewed by 1367
Abstract
In this study, an iridium-catalyzed selective 1,4-reduction of α,β-unsaturated carbonyl compounds is realized, with water as a solvent and formic acid as a hydride donor. The new efficient iridium catalyst features a 2-(4,5-dihydroimidazol-2-yl)quinoline ligand. The chemoselectivity and catalyst efficiency are highly dependent on [...] Read more.
In this study, an iridium-catalyzed selective 1,4-reduction of α,β-unsaturated carbonyl compounds is realized, with water as a solvent and formic acid as a hydride donor. The new efficient iridium catalyst features a 2-(4,5-dihydroimidazol-2-yl)quinoline ligand. The chemoselectivity and catalyst efficiency are highly dependent on the electronic and steric properties of the substrates. For α,β-unsaturated amides, acids, and esters, only the electron-deficient C=C bonds are reduced (1,4-reduction), and the other functional groups are left intact. The S/C ratio and initial TOF reach 7000 and 18,480 h−1, respectively. A gram-scale 1,4-reduction is also performed. Deuterium labeling shows that the β-hydrogens of the products originate from the formyl hydrogen in the formic acid. The application of the 1,4-reduction for the modification the structures of some medications is demonstrated. Full article
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