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Copper in Synthesis and Catalysis
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Copper in Synthesis and Catalysis

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

Deadline for manuscript submissions: closed (28 February 2022) | Viewed by 19503

Special Issue Editors

Dr. Dzmitry Kananovich

E-Mail Website
Guest Editor
Tallinna Tehnikaülikool, Tallinn, Estonia
Interests: organic synthesis; medicinal and pharmaceutical chemistry; organometallic synthesis
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Zhuofeng Ke

E-Mail Website
Guest Editor
School of Materials Science and Engineering, PCFM Lab, Sun Yat-sen University, Guangzhou 510275, China
Interests: sustainable catalysis; computational chemistry; organometallics; green synthesis; chemical fuels
Prof. Dr. Xinfang Xu

E-Mail Website
Guest Editor
Guangdong Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, Guangdong, China
Interests: asymmetric catalysis; methodology development; leading compounds discovery; metal carbene; heterocycles

Special Issue Information

Dear Colleagues,

The current need for sustainable development has spurred a remarkable research activity in the field of chemical synthesis and catalysis with earth-abundant transition metals.

Copper and its compounds are readily available, representing one of the first metals known to humankind. The history of transition metal catalysis in organic chemistry also started with a copper-catalyzed homo-coupling of alkynes, discovered by Carl Glazer in 1869. Since then, copper-containing materials have acquired an impressive track record as catalysts in organic synthesis, including various carbon–carbon and carbon–heteroatom cross-coupling reactions, aerobic oxidations, trifluoromethylations, etc. Numerous asymmetric transformations mediated by chiral copper complexes have been developed. Furthermore, coordination chemistry of copper is essential for self-assembly of intricate supramolecular structures and metal–organic frameworks (MOFs).

The goal of this Special Issue is to collect original research papers and review articles devoted to all aspects of modern copper chemistry and its uses in organic synthesis, catalysis, chemical sensing, and innovative separation techniques. Submission of manuscripts describing preparation of new copper-containing materials with applications in various areas of chemical science and technology is also encouraged.

Dr. Dzmitry Kananovich
Prof. Dr. Zhuofeng Ke
Prof. Dr. Xinfang Xu
Guest Editors

Manuscript Submission Information

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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. Molecules is an international peer-reviewed open access semimonthly 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 2700 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

  • Copper
  • Transition metals
  • Organic synthesis
  • Coordination chemistry
  • Organometallics
  • Metal complexes
  • Homogeneous catalysis
  • Heterogeneous catalysis
  • New synthetic methods
  • Enantioselective synthesis
  • Chirality
  • Chemical sensors
  • Metal–organic frameworks
  • Mechanistic studies
  • Green chemistry
  • Sustainable development

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Published Papers (6 papers)

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Research

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16 pages, 5676 KiB  
Article
Development of Functional Composite Cu(II)-Polyoxometalate/PLA with Antimicrobial Properties
by Ella Duvanova, Illia Krasnou, Andres Krumme, Valdek Mikli, Serhii Radio, Georgiy M. Rozantsev and Yevgen Karpichev
Molecules 2022, 27(8), 2510; https://doi.org/10.3390/molecules27082510 - 13 Apr 2022
Cited by 5 | Viewed by 2680
Abstract
Novel composite self-disinfecting films of polylactic acid (PLA) filled with nanosized particles of double sodium–copper(II) paratungstate B Na2Cu3(CuOH)2[W12O40(OH)2]·32H2O (POM) were developed. The solvent casting (POM/PLA film) and solvent-free melt [...] Read more.
Novel composite self-disinfecting films of polylactic acid (PLA) filled with nanosized particles of double sodium–copper(II) paratungstate B Na2Cu3(CuOH)2[W12O40(OH)2]·32H2O (POM) were developed. The solvent casting (POM/PLA film) and solvent-free melt extrusion methods (Extr. POM/PLA film) were applied for film preparation. The copper (II) ion release to water from both types of the films after 10 days at different temperatures demonstrated that the PLA matrix acts as a diffusion barrier, and the resulting concentration of released copper in water at room temperature remained low, at 0.79% for POM/PLA film and 0.51% for Extr. POM/PLA film. The POM-containing films reveals a significant inhibitory effect against E. coli ATCC 25922 in the agar diffusion test. The numbers of CFUs in washes of the films after incubation for 24 h were found to be 3.6 log CFU mL–1 (POM/PLA film) and 4.1 log CFU mL–1 (Extr. POM/PLA film). The films combine the antibacterial properties of POM and a bio-based polymer matrix, which makes them a prospective coating material for applications in hospital indoor environments. Excellent thermal stability of POM gives a technological advantage for industrial manufacturing to allow the processing of novel composite material in the solvent free (molten) state. Full article
(This article belongs to the Special Issue Copper in Synthesis and Catalysis)
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18 pages, 1320 KiB  
Article
Mild Copper-Catalyzed, l-Proline-Promoted Cross-Coupling of Methyl 3-Amino-1-benzothiophene-2-carboxylate
by Vilija Kederienė, Indrė Jaglinskaitė, Paulina Voznikaitė, Jolanta Rousseau, Patrick Rollin, Algirdas Šačkus and Arnaud Tatibouët
Molecules 2021, 26(22), 6822; https://doi.org/10.3390/molecules26226822 - 11 Nov 2021
Cited by 3 | Viewed by 2597
Abstract
Cu-catalyzed N-arylation is a useful tool for the chemical modification of aromatic heterocycles. Herein, an efficient carbon–nitrogen cross-coupling of methyl 3-amino-1-benzothiophene-2-carboxylate with a range of (hetero)aryl iodides using CuI, l-proline and Cs2CO3 in dioxane at moderate temperature is [...] Read more.
Cu-catalyzed N-arylation is a useful tool for the chemical modification of aromatic heterocycles. Herein, an efficient carbon–nitrogen cross-coupling of methyl 3-amino-1-benzothiophene-2-carboxylate with a range of (hetero)aryl iodides using CuI, l-proline and Cs2CO3 in dioxane at moderate temperature is described. The procedure is an extremely general, relatively cheap, and experimentally simple way to afford the N-substituted products in moderate to high yields. The structures of the new heterocyclic compounds were confirmed by NMR spectroscopy and HRMS investigation. Full article
(This article belongs to the Special Issue Copper in Synthesis and Catalysis)
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16 pages, 1610 KiB  
Article
A New Dimeric Copper(II) Complex of Hexyl Bis(pyrazolyl)acetate Ligand as an Efficient Catalyst for Allylic Oxidations
by Luca Bagnarelli, Alessandro Dolmella, Carlo Santini, Riccardo Vallesi, Roberto Giacomantonio, Serena Gabrielli and Maura Pellei
Molecules 2021, 26(20), 6271; https://doi.org/10.3390/molecules26206271 - 16 Oct 2021
Cited by 3 | Viewed by 2987
Abstract
A new dimeric copper(II) bromide complex, [Cu(LOHex)Br(μ-Br)]2 (1), was prepared by a reaction of CuBr2 with the hexyl bis(pyrazol-1-yl)acetate ligand (LOHex) in acetonitrile solution and fully characterized in the solid state and in solution. The [...] Read more.
A new dimeric copper(II) bromide complex, [Cu(LOHex)Br(μ-Br)]2 (1), was prepared by a reaction of CuBr2 with the hexyl bis(pyrazol-1-yl)acetate ligand (LOHex) in acetonitrile solution and fully characterized in the solid state and in solution. The crystal structure of 1 was also determined: the complex is interlinked by two bridging bromide ligands and possesses terminal bromide ligands on each copper atom. The two pyrazolyl ligands in 1 coordinate with the nitrogen atoms to complete the Cu coordination sphere, resulting in a five-coordinated geometry—away from idealized trigonal bipyramidal and square pyramidal geometries—which can better be described as distorted square pyramidal, as measured by the τ and χ structural parameters. The pendant hexyloxy chain is disordered over two arrangements, with final site occupancies refined to 0.705 and 0.295. The newly synthesized complex was evaluated as a catalyst in copper-catalyzed C–H oxidation for allylic functionalization through a Kharasch–Sosnovsky reaction without any external reducing agent. Using 0.5 mol% of this catalyst, and tert-butyl peroxybenzoate (Luperox) as an oxidant, allylic benzoates were obtained with up to 90% yield. The general reaction time was only slightly decreased to 24 h but a very significant decrease in the alkene:Luperox ratio to 3:1 was achieved. These factors show relevant improvements with respect to classical Kharasch–Sosnovsky reactions in terms of rate and amount of reagents. The present study highlights the potential of copper(II) complexes containing functionalized bis(pyrazol-1-yl)acetate ligands as efficient catalysts for allylic oxidations. Full article
(This article belongs to the Special Issue Copper in Synthesis and Catalysis)
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12 pages, 8051 KiB  
Article
Reversal of Enantioselectivity in the Conjugate Addition Reaction of Cyclic Enones with the CuOTf/Azolium Catalytic System
by Yuki Nakano, Satoki Shimizu, Chihiro Takeda and Satoshi Sakaguchi
Molecules 2021, 26(11), 3404; https://doi.org/10.3390/molecules26113404 - 4 Jun 2021
Cited by 1 | Viewed by 2336
Abstract
Hydroxyamide-functionalized azolium salt (NHC•HI 4) was evaluated for dual enantioselective control in a Cu-catalyzed asymmetric conjugate addition (ACA) reaction. This investigation was based on our previously reported ACA reaction catalyzed using CuOTf combined with NHC•AgI complex 1. It was revealed that [...] Read more.
Hydroxyamide-functionalized azolium salt (NHC•HI 4) was evaluated for dual enantioselective control in a Cu-catalyzed asymmetric conjugate addition (ACA) reaction. This investigation was based on our previously reported ACA reaction catalyzed using CuOTf combined with NHC•AgI complex 1. It was revealed that the stereocontrol of the catalytic ACA reaction depended on the order of the addition of the substrates. Additionally, the chiral NHC ligand precursors, substrates, the relationship between the catalyst ee (eecat) and product ee (eepro), and halogen counter anion were completely evaluated. These results suggested that the catalytic performance of the CuOTf/4 system was comparable with that of the CuOTf/1 system. Furthermore, to gain knowledge of the Cu species generated using CuOTf and NHC ligand precursor, the reaction of CuOTf with 1 was investigated. Although obtaining the corresponding NHC•CuX species failed, the corresponding NHC•AuCl complex 11 could be synthesized by allowing 1 to react with AuCl•SMe2. Full article
(This article belongs to the Special Issue Copper in Synthesis and Catalysis)
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Review

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1 pages, 9766 KiB  
Review
Updated Progress of the Copper-Catalyzed Borylative Functionalization of Unsaturated Molecules
by Bingru Li, Huayu Liang, Arumugam Vignesh, Xiaoyu Zhou, Yan Liu and Zhuofeng Ke
Molecules 2023, 28(5), 2252; https://doi.org/10.3390/molecules28052252 - 28 Feb 2023
Cited by 15 | Viewed by 3299
Abstract
Borylation has become a powerful method to synthesize organoboranes as versatile building blocks in organic synthesis, medicinal chemistry, and materials science. Copper-promoted borylation reactions are extremely attractive due to the low cost and non-toxicity of the copper catalyst, mild reaction conditions, good functional [...] Read more.
Borylation has become a powerful method to synthesize organoboranes as versatile building blocks in organic synthesis, medicinal chemistry, and materials science. Copper-promoted borylation reactions are extremely attractive due to the low cost and non-toxicity of the copper catalyst, mild reaction conditions, good functional group tolerance, and convenience in chiral induction. In this review, we mainly updated recent advances (from 2020 to 2022) in the synthetic transformations in C=C/C≡C multiple bonds, and C=E multiple bonds mediated by copper boryl systems. Full article
(This article belongs to the Special Issue Copper in Synthesis and Catalysis)
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25 pages, 6240 KiB  
Review
Recent Advances in Catalytic Alkyne Transformation via Copper Carbene Intermediates
by Kuiyong Dong, Mengting Liu and Xinfang Xu
Molecules 2022, 27(10), 3088; https://doi.org/10.3390/molecules27103088 - 11 May 2022
Cited by 20 | Viewed by 4256
Abstract
As one of the abundant and inexpensive metals on the earth, copper has demonstrated broad applications in synthetic chemistry and catalysis. Among these copper-catalyzed advances, copper carbenes are versatile and reactive intermediates that can mediate a variety of transformations, which have attracted much [...] Read more.
As one of the abundant and inexpensive metals on the earth, copper has demonstrated broad applications in synthetic chemistry and catalysis. Among these copper-catalyzed advances, copper carbenes are versatile and reactive intermediates that can mediate a variety of transformations, which have attracted much attention in the past decades. The present review summarizes two different reaction models that take place between a copper carbene intermediate and alkyne species, including the cross-coupling reaction of copper carbene intermediate with terminal alkyne, and the addition of copper carbene intermediate onto the C–C triple bond. This article will cover the profile from 2010 to 2021 by placing emphasis on the detailed catalytic models and highlighting the synthetic applications offered by these practical and mild methods. Full article
(This article belongs to the Special Issue Copper in Synthesis and Catalysis)
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