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Metal-Catalyzed Organic Transformations: Expanding Horizons in Synthetic Methodology

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

Deadline for manuscript submissions: 30 September 2025 | Viewed by 12326

Special Issue Editor


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Guest Editor
College of Chemistry, Tianjin Normal University, Tianjin, China
Interests: palladium catalysis; cyclization reaction; green chemistry; domino reaction; free radical chemistry

Special Issue Information

Dear Colleagues,

Metal-catalyzed organic transformations are crucial tools for synthesizing complex molecules, as they enhance the efficiency of chemical reactions, streamline the synthetic pathways, and reduce the production costs. Therefore, it is essential to develop highly efficient synthetic transformations to construct bioactive molecules using metal catalysis. This Special Issue aims to encompass a comprehensive overview of the latest advancements in metal-catalyzed organic transformations. The Guest Editor invites reviews and original research articles that explore the diverse and expanding horizons of synthetic methodology enabled by metal catalysts. The topics encompass innovative strategies used to construct complex molecules, efficient synthetic pathways, and the synthesis of bioactive compounds. This collection serves as a valuable resource for researchers seeking to stay abreast of the latest developments in metal-catalyzed organic transformations and their impact on synthetic chemistry.

Dr. Chen Chen
Guest Editor

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Keywords

  • multicomponent reactions
  • transition metal catalysis
  • organometallic chemistry
  • electrosynthesis
  • photocatalysis
  • green organic synthesis
  • bioactive molecules

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Published Papers (9 papers)

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Research

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13 pages, 1994 KiB  
Article
Exploring the Photocatalytic Efficiency of Gold Nanoparticles Deposited on Ni-Al-Zr-Layered Double Hydroxides for Selective Glucose Oxidation
by Nihel Dib, Frédéric Sauvage, Lucie Quéhon, Khadidja Khaldi, Sumeya Bedrane, José Juan Calvino, Redouane Bachir, Ginesa Blanco and Gwladys Pourceau
Molecules 2025, 30(1), 13; https://doi.org/10.3390/molecules30010013 - 24 Dec 2024
Viewed by 710
Abstract
Confronting escalating challenges in energy security and environmental sustainability has intensified interest in renewable sources for fuels and chemicals. Among the most promising alternatives, sugars derived from biomass are emerging as a cornerstone in advancing an environmentally sustainable economy. Within this framework, the [...] Read more.
Confronting escalating challenges in energy security and environmental sustainability has intensified interest in renewable sources for fuels and chemicals. Among the most promising alternatives, sugars derived from biomass are emerging as a cornerstone in advancing an environmentally sustainable economy. Within this framework, the development of sunlight-driven carbohydrate oxidation is of significant interest, as it enables the production of a broad spectrum of high-value, bio-sourced chemicals through eco-friendly processes. Gold nanoparticles (Au NPs) immobilized on inorganic supports have demonstrated considerable potential in this area, although the methodology still requires further exploration. In this study, we explored the selective oxidation of glucose into the corresponding gluconic acid salt in presence of a novel Au/Ni-Al-Zr-layered double hydroxide (LDH) photocatalyst under standardized A.M. 1.5 G light illumination. To optimize the photocatalytic conditions, an experimental plan is herein proposed, highlighting the critical influences of both catalyst loading and pH. In optimal conditions, the Au catalyst demonstrated a high efficiency, achieving 87% glucose conversion and 100% selectivity towards gluconic acid in only 90 min. By means of long-pass filters to select the incident light energy to the photocatalytic reactor, we evidenced that the charge transfer processes were occurring from the Ni-Al-Zr LDH support to the gold nanoparticles, thus opening new directions towards further photocatalyst modifications. This work underlines the potential of Au/LDH materials for sunlight-driven photocatalysis and provides a pathway for the sustainable production of high-value chemicals from renewable biomass sources. Full article
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14 pages, 2005 KiB  
Article
Selectivity Control in Nitroaldol (Henry) Reaction by Changing the Basic Anion in a Chiral Copper(II) Complex Based on (S)-2-Aminomethylpyrrolidine and 3,5-Di-tert-butylsalicylaldehyde
by Olga V. Khromova, Lidiya V. Yashkina, Nadezhda V. Stoletova, Victor I. Maleev, Yuri N. Belokon and Vladimir A. Larionov
Molecules 2024, 29(21), 5207; https://doi.org/10.3390/molecules29215207 - 4 Nov 2024
Viewed by 1221
Abstract
This article is a continuation of our previous research on the catalytic capability of a chiral copper complex based on commercially available (S)-2-aminomethylpyrrolidine and 3,5-di-tert-butylsalicylaldehyde with various counter-anions in the asymmetric Henry reaction. Our findings indicate that depending on [...] Read more.
This article is a continuation of our previous research on the catalytic capability of a chiral copper complex based on commercially available (S)-2-aminomethylpyrrolidine and 3,5-di-tert-butylsalicylaldehyde with various counter-anions in the asymmetric Henry reaction. Our findings indicate that depending on the type of base used, chiral nitroalcohols with yields up to 98% and ee values up to 77%, as well as β-nitrostyrenes with yields up to 88%, can be produced. Additionally, it has been found that the outcome of the reaction and the catalytic properties of copper (II) complexes (S)-Cu1 and (S)-Cu2 are influenced by the structure of the aldehyde used. Full article
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15 pages, 14229 KiB  
Article
Trade-Off between Degradation Efficiency and Recyclability: Zeolite-Enhanced Ni3−xCoxS4 Catalyst for Photocatalytic Degradation of Methylene Blue
by Rachel Anne E. Lagunay, Ritche Roi B. Adalim, Aruzhan Tleubekova, Diana Suleimenova, Marvin Jose F. Fernandez, Robert J. O’Reilly and Mannix P. Balanay
Molecules 2024, 29(17), 4167; https://doi.org/10.3390/molecules29174167 - 3 Sep 2024
Viewed by 1324
Abstract
We herein report successful syntheses of both nickel cobalt sulfide (NCS) and its composite with zeolite (NCS@Z) using a solvothermal method. Techniques such as EDX analysis, SEM, and molar ratio determination were used for product characterization. The incorporation of NCS significantly changed the [...] Read more.
We herein report successful syntheses of both nickel cobalt sulfide (NCS) and its composite with zeolite (NCS@Z) using a solvothermal method. Techniques such as EDX analysis, SEM, and molar ratio determination were used for product characterization. The incorporation of NCS significantly changed the surface roughness and active sites of the zeolite, improving the efficiency of methylene blue degradation and its reusability, especially under UV irradiation. In comparing the pseudo-first order rates, the highest degradation efficiency of methylene blue was achieved with NCS-2@Z, having a degradation extent of 91.07% under UV irradiation. This environmentally friendly approach offers a promising solution for the remediation of methylene blue contamination in various industries. Full article
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12 pages, 1557 KiB  
Article
Pallado-Catalyzed Cascade Synthesis of 2-Alkoxyquinolines from 1,3-Butadiynamides
by Illia Lenko, Alexander Mamontov, Carole Alayrac and Bernhard Witulski
Molecules 2024, 29(15), 3505; https://doi.org/10.3390/molecules29153505 - 26 Jul 2024
Viewed by 912
Abstract
A novel synthesis strategy to access 2-alkoxyquinoline derivatives via a palladium-driven cascade reaction is disclosed. Unlike classic methods based on the alkylation of 2-quinolones with alkyl halides, the present method benefits from the de novo assembly of the quinoline core starting from 1,3-butadiynamides. [...] Read more.
A novel synthesis strategy to access 2-alkoxyquinoline derivatives via a palladium-driven cascade reaction is disclosed. Unlike classic methods based on the alkylation of 2-quinolones with alkyl halides, the present method benefits from the de novo assembly of the quinoline core starting from 1,3-butadiynamides. Palladium-catalyzed reaction cascades with N-(2-iodophenyl)-N-tosyl-1,3-butadiynamides and primary alcohols as external nucleophiles proceed under mild reaction conditions and selectively deliver a variety of differently functionalized 4-alkenyl 2-alkoxyquinolines in a single batch transformation. Full article
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16 pages, 3215 KiB  
Article
P(V)-Promoted Rh-Catalyzed Highly Regioselective Hydroformylation of Styrenes under Mild Conditions
by Tong Ru, Yajiao Zhang, Qiuxiang Wei, Sheng Zuo, Zhenhua Jia and Fen-Er Chen
Molecules 2024, 29(9), 2039; https://doi.org/10.3390/molecules29092039 - 28 Apr 2024
Cited by 1 | Viewed by 1542
Abstract
Hydroformylation of olefins is widely used in the chemical industry due to its versatility and the ability to produce valuable aldehydes with 100% atom economy. Herein, a hybrid phosphate promoter was found to efficiently promote rhodium-catalyzed hydroformylation of styrenes under remarkably mild conditions [...] Read more.
Hydroformylation of olefins is widely used in the chemical industry due to its versatility and the ability to produce valuable aldehydes with 100% atom economy. Herein, a hybrid phosphate promoter was found to efficiently promote rhodium-catalyzed hydroformylation of styrenes under remarkably mild conditions with high regioselectivities. Preliminary mechanistic studies revealed that the weak coordination between the Rhodium and the P=O double bond of this pentavalent phosphate likely induced exceptional reactivity and high ratios of branched aldehydes to linear products. Full article
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13 pages, 1869 KiB  
Communication
Photoinduced Site-Selective Aryl C-H Borylation with Electron-Donor-Acceptor Complex Derived from B2Pin2 and Isoquinoline
by Manhong Li, Yi-Hui Deng, Qianqian Chang, Jinyuan Li, Chao Wang, Leifeng Wang and Tian-Yu Sun
Molecules 2024, 29(8), 1783; https://doi.org/10.3390/molecules29081783 - 14 Apr 2024
Cited by 1 | Viewed by 2244
Abstract
Due to boron’s metalloid properties, aromatic boron reagents are prevalent synthetic intermediates. The direct borylation of aryl C-H bonds for producing aromatic boron compounds offers an appealing, one-step solution. Despite significant advances in this field, achieving regioselective aryl C-H bond borylation using simple [...] Read more.
Due to boron’s metalloid properties, aromatic boron reagents are prevalent synthetic intermediates. The direct borylation of aryl C-H bonds for producing aromatic boron compounds offers an appealing, one-step solution. Despite significant advances in this field, achieving regioselective aryl C-H bond borylation using simple and readily available starting materials still remains a challenge. In this work, we attempted to enhance the reactivity of the electron-donor-acceptor (EDA) complex by selecting different bases to replace the organic base (NEt3) used in our previous research. To our delight, when using NH4HCO3 as the base, we have achieved a mild visible-light-mediated aromatic C-H bond borylation reaction with exceptional regioselectivity (rr > 40:1 to single isomers). Compared with our previous borylation methodologies, this protocol provides a more efficient and broader scope for aryl C-H bond borylation through the use of N-Bromosuccinimide. The protocol’s good functional-group tolerance and excellent regioselectivity enable the functionalization of a variety of biologically relevant compounds and novel cascade transformations. Mechanistic experiments and theoretical calculations conducted in this study have indicated that, for certain arenes, the aryl C-H bond borylation might proceed through a new reaction mechanism, which involves the formation of a novel transient EDA complex. Full article
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16 pages, 2692 KiB  
Article
tert-Butyl Nitrite-Induced Radical Nitrile Oxidation Cycloaddition: Synthesis of Isoxazole/Isoxazoline-Fused Benzo 6/7/8-membered Oxacyclic Ketones
by Jian-Kang Cao, Tian-Zheng Cao, Qian-Wen Yue, Ying Ma, Chuan-Ming Yang, Hong-Xi Zhang, Ya-Chen Li, Qiao-Ke Dong, Yan-Ping Zhu and Yuan-Yuan Sun
Molecules 2024, 29(6), 1202; https://doi.org/10.3390/molecules29061202 - 7 Mar 2024
Cited by 1 | Viewed by 1778
Abstract
A practical metal-free and additive-free approach for the synthesis of 6/7/8-membered oxacyclic ketone-fused isoxazoles/isoxazolines tetracyclic or tricyclic structures is reported through Csp3–H bond radical nitrile oxidation and the intramolecular cycloaddition of alkenyl/alkynyl-substituted aryl methyl ketones. This convenient approach enables the [...] Read more.
A practical metal-free and additive-free approach for the synthesis of 6/7/8-membered oxacyclic ketone-fused isoxazoles/isoxazolines tetracyclic or tricyclic structures is reported through Csp3–H bond radical nitrile oxidation and the intramolecular cycloaddition of alkenyl/alkynyl-substituted aryl methyl ketones. This convenient approach enables the simultaneous formation of isoxazole/isoxazoline and 6/7/8-membered oxacyclic ketones to form polycyclic architectures by using tert-butyl nitrite (TBN) as a non-metallic radical initiator and N–O fragment donor. Full article
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12 pages, 1737 KiB  
Article
Enhanced Selectivity in 4-Quinolone Formation: A Dual-Base System for Palladium-Catalyzed Carbonylative Cyclization with Fe(CO)5
by Meng Guo, Dou Wu, Hongyu Yang, Xiao Zhang, Dong-Xu Xue and Weiqiang Zhang
Molecules 2024, 29(4), 850; https://doi.org/10.3390/molecules29040850 - 14 Feb 2024
Cited by 1 | Viewed by 1108
Abstract
The use of gaseous CO in Pd-catalyzed carbonylative quinolone synthesis presents challenges related to safety and precise pressure control. In response, a streamlined non-gaseous synthesis of 4-quinolone compounds has been developed. This study introduces a tunable CO-releasing system utilizing Fe(CO)5 activated by [...] Read more.
The use of gaseous CO in Pd-catalyzed carbonylative quinolone synthesis presents challenges related to safety and precise pressure control. In response, a streamlined non-gaseous synthesis of 4-quinolone compounds has been developed. This study introduces a tunable CO-releasing system utilizing Fe(CO)5 activated by a dual-base system of piperazine and triethylamine. This alternative liquid CO resource facilitates the palladium-catalyzed carbonylative C-C coupling and subsequent intramolecular cyclization. By tuning the tandem kinetics of carbonylation and cyclization, this non-gaseous method achieves the successful synthesis of 22 distinct 4-quinolones with excellent yields. This is achieved through the three-component condensation of sub-stoichiometric amounts of Fe(CO)5 with 2-iodoaniline and terminal alkynes. Operando mechanistic studies have revealed a novel CO transfer mechanism that facilitates homogeneous carbonylative cyclization, distinguishing this method from traditional techniques. In addition to addressing safety concerns, this approach also provides precise control over selectivity, with significant implications for pharmaceutical research and the efficient synthesis of pharmaceutical and bioactive compounds. Full article
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Review

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44 pages, 115423 KiB  
Review
Research Progress in Epoxidation of Light Small-Molecule Olefins
by Guanghui Zhao, Tianfu Yang, Jincheng Liu, Xianming Xu, Yulong Wang, Yongjun Zhang, Meng Gao, Chao Xiong and Hongbing Ji
Molecules 2025, 30(6), 1340; https://doi.org/10.3390/molecules30061340 - 17 Mar 2025
Viewed by 516
Abstract
Light olefins, as important bulk raw materials in the petrochemical industry, play an irreplaceable role in the development of the manufacturing industry and the economy. The epoxides of light olefins are important intermediates for the synthesis of polymers, drugs, and fine chemicals, and [...] Read more.
Light olefins, as important bulk raw materials in the petrochemical industry, play an irreplaceable role in the development of the manufacturing industry and the economy. The epoxides of light olefins are important intermediates for the synthesis of polymers, drugs, and fine chemicals, and their green, efficient, and safe synthesis has attracted much attention. This review focuses on the research progress of light olefin epoxidation and elucidates traditional epoxidation methods, such as the chlorohydrin method. Although these processes have mature processes, they have drawbacks, including equipment corrosion, environmental pollution, poor safety, and high waste emissions. Special emphasis is placed on catalytic epoxidation systems using oxygen or organic peroxides as oxygen sources. For homogeneous catalytic systems, certain metal complexes exhibit high activity and selectivity yet are difficult to separate and recycle. Moreover, heterogeneous catalytic systems have become a research hotspot due to their advantages of easy separation and reusability, with supported metal catalysts being a prime example. Meanwhile, the effects of reaction temperature, pressure, solvent, etc., on epoxidation are explored. The specific reaction mechanisms are also studied and analyzed. Current research challenges, including enhancing catalyst stability and reducing costs, are summarized. In the future, developing highly efficient, green, and economically viable epoxidation technologies for large-scale industrial applications represents an important research direction in this field. Full article
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