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New Insights in Coupling Reactions

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

Deadline for manuscript submissions: closed (30 April 2023) | Viewed by 8666

Special Issue Editors


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Guest Editor
Graduate School of Pharmaceutical Sciences, Ritsumeikan University, Shiga 525-8577, Japan
Interests: hypervalent iodine chemistry and its application; oxidation; coupling; heterocycle synthesis; asymmetric synthesis
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Guest Editor
Department of Biomolecular Sciences, University of Urbino “Carlo Bo”, 61029 Urbino, Italy
Interests: organic synthesis; heterocyclic chemistry; C-H activation; cyclization; michael addition; photochemistry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

The transition metal-catalyzed cross-coupling strategy established in 20th century has become an important tool to create a carbon–carbon bond for the target molecules, which now encompass a range of aryl, alkynyl, and alkenyl substrates as counterpart of organometallic nucleophiles. These cross-coupling methods are known to be particularly useful for both laboratorial and industrial synthesis of building blocks for biologically active compounds and organic materials. Aiming at further advances and application of cross-coupling synthesis, new research on academic and industrial developments has appeared on a regular basis.

The classical cross-coupling strategy would rely on the use of aryl halides (X = I, Br, Cl) and aryl metallic compounds (e.g., [M] = [Zn]: Negishi, [B]: Suzuki-Miyaura, [Sn]: Stille) in employing transition metal catalysts, such as palladium complex, while inspired by the concept of green and sustainable chemistry, more direct C–H functionalization using organic halides or organometallic compounds as one of these coupling partner was suggested in the past decade. Furthermore, through the success of controlling the oxidative cross-coupling selectivities, the most ideal synthetic route in view of the green chemistry that directly uses two molecules of C–H groups for a new bond-forming event has been realized in recent years, even for sp3 C–H bonds.

This Special Issue aim to highlight recent trends and new insights in advancing cross-couplings with estimating their continuous developments in future. The guest editors welcome review and original research articles associated with recent achievements in this area, regarding catalysts, substrates, reaction systems, etc. Areas to be covered in this Special Issue may include but are not limited to the extension of the known synthetic strategy and application to the useful organic compounds, i.e., bioactive molecules and organic materials. Indeed, promising new synthetic applications targeting the very difficult functionalizations of aqueous biological macromolecules, such as peptides and DNAs, have been found in recent drug discovery studies.

As guest editors, we hope that this Special Issue will inspire authors and readers as much as the researchers engaged in this area.

Prof. Dr. Toshifumi Dohi
Prof. Dr. Gianfranco Favi
Guest Editors

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Keywords

  • coupling
  • catalysts
  • C–X and hetero-X functionalizations
  • C–H activations
  • C–H functionalizations
  • organic materials
  • pharmaceutical compounds
  • heterocycles
  • heteroaromatic compounds
  • biological molecules

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Published Papers (3 papers)

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Research

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10 pages, 8423 KiB  
Communication
Palladium-Catalyzed Synthesis of Cyclopropylthiophenes and Their Derivatization
by Tomas Paškevičius, Ringailė Lapinskaitė, Sigitas Stončius, Rita Sadzevičienė, Asta Judžentienė and Linas Labanauskas
Molecules 2023, 28(9), 3770; https://doi.org/10.3390/molecules28093770 - 27 Apr 2023
Viewed by 1387
Abstract
The cyclopropylthiophene moiety has attracted the attention of the scientific community for its potential pharmaceutical applications. However, synthesis of the compounds containing this framework remains challenging, has rarely been reported and remains unresolved. Here we provide optimized syntheses for cyclopropylthiophenes and their derivatives, [...] Read more.
The cyclopropylthiophene moiety has attracted the attention of the scientific community for its potential pharmaceutical applications. However, synthesis of the compounds containing this framework remains challenging, has rarely been reported and remains unresolved. Here we provide optimized syntheses for cyclopropylthiophenes and their derivatives, containing carbonyl, acetyl, carboxylic acid, methyl carboxylate, nitrile, bromide and sulfonyl chloride moieties. Full article
(This article belongs to the Special Issue New Insights in Coupling Reactions)
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17 pages, 1504 KiB  
Article
Copper-catalyzed S-arylation of Furanose-Fused Oxazolidine-2-thiones
by Vilija Kederienė, Jolanta Rousseau, Marie Schuler, Algirdas Šačkus and Arnaud Tatibouët
Molecules 2022, 27(17), 5597; https://doi.org/10.3390/molecules27175597 - 30 Aug 2022
Cited by 2 | Viewed by 1717
Abstract
The 1,3-oxazolidine-2-thiones (OZTs) are important chiral molecules, especially in asymmetric synthesis. These compounds serve as important active units in biologically active compounds. Herein, carbohydrate anchored OZTs were explored to develop a copper-catalyzed C-S bond formation with aryl iodides. Chemoselective S-arylation was observed, [...] Read more.
The 1,3-oxazolidine-2-thiones (OZTs) are important chiral molecules, especially in asymmetric synthesis. These compounds serve as important active units in biologically active compounds. Herein, carbohydrate anchored OZTs were explored to develop a copper-catalyzed C-S bond formation with aryl iodides. Chemoselective S-arylation was observed, with copper iodide and dimethylethylenediamine (DMEDA) as the best ligand in dioxane at 60–90 °C. The corresponding chiral oxazolines were obtained in reasonable to good yields under relatively mild reaction conditions. This approach is cheap, as using one of the cheapest transition metals, a simple protocol and various functional group tolerance make it a valuable strategy for getting S-substituted furanose-fused OZT. The structures of the novel carbohydrates were confirmed by NMR spectroscopy and an HRMS analysis. Full article
(This article belongs to the Special Issue New Insights in Coupling Reactions)
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Review

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53 pages, 10642 KiB  
Review
Transition Metal Catalyzed Hiyama Cross-Coupling: Recent Methodology Developments and Synthetic Applications
by Rida Noor, Ameer Fawad Zahoor, Muhammad Irfan, Syed Makhdoom Hussain, Sajjad Ahmad, Ali Irfan, Katarzyna Kotwica-Mojzych and Mariusz Mojzych
Molecules 2022, 27(17), 5654; https://doi.org/10.3390/molecules27175654 - 2 Sep 2022
Cited by 9 | Viewed by 4635
Abstract
Hiyama cross-coupling is a versatile reaction in synthetic organic chemistry for the construction of carbon–carbon bonds. It involves the coupling of organosilicons with organic halides using transition metal catalysts in good yields and high enantioselectivities. In recent years, hectic progress has been made [...] Read more.
Hiyama cross-coupling is a versatile reaction in synthetic organic chemistry for the construction of carbon–carbon bonds. It involves the coupling of organosilicons with organic halides using transition metal catalysts in good yields and high enantioselectivities. In recent years, hectic progress has been made by researchers toward the synthesis of diversified natural products and pharmaceutical drugs using the Hiyama coupling reaction. This review emphasizes the recent synthetic developments and applications of Hiyama cross-coupling. Full article
(This article belongs to the Special Issue New Insights in Coupling Reactions)
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