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Catalysts
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Advances in Catalytic Coupling Reactions
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Advances in Catalytic Coupling Reactions

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 (10 February 2022) | Viewed by 25682

Special Issue Editors

Prof. Dr. Igor M. Opsenica

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Guest Editor
Faculty of Chemistry, University of Belgrade, Belgrade, Serbia
Interests: organic catalysts
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Hironao Sajiki

E-Mail Website
Guest Editor
Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan
Interests: coupling reaction; catalysis; environmental catalysis; hydrogenation; H–D exchange reaction
Special Issues, Collections and Topics in MDPI journals
Dr. Yoshinari Sawama

E-Mail Website
Guest Editor
Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan
Interests: heterogeneous catalyst; Lewis acid, metal free; H-D exchange reaction; total synthesis of natural products
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Coupling reactions are a fundamental and reliable organic synthetic tool for constructing carbon–carbon, carbon–nitrogen, and carbon–oxygen bonds in various academic and industrial fields. For example, the Suzuki–Miyaura cross-coupling reaction between an aryl halide and an organoboron species is catalyzed by the combination of a palladium metal catalyst and a ligand to form a carbon–carbon bond. Until today, various improvements have been made to transition metal catalysts and ligands, and reaction efficiencies and substrate applicability have been dramatically improved. With advances in reactors and technologies, reaction efficiencies are further enhanced by introducing novel techniques such as microwave and flow systems.

This Special Issue focuses on the modernization of various catalytic coupling reactions, such as carbon–carbon, carbon–heteroatom (nitrogen, oxygen, sulfur, etc.) bond formation. We welcome articles, communications, and reviews on the recent advances in coupling reactions using homogeneous/heterogeneous catalysts, and traditional/renovated/novel reaction methods, equipment and technology.

Prof. Dr. Igor M. Opsenica
Prof. Dr. Hironao Sajiki
Dr. Yoshinari Sawama
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

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. Catalysts is an international peer-reviewed open access monthly 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 2200 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

  • coupling reaction (regarding C–C, C–N, C–O, etc. bond formation)
  • recent advances in batch, microwave, and flow reactor systems
  • catalyst design
  • heterogeneous or homogeneous catalysts
  • traditional, renovated, or novel techniques
  • know-how

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Related Special Issue

Published Papers (5 papers)

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Research

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21 pages, 11457 KiB  
Article
Combustion-Synthesized Porous CuO-CeO2-SiO2 Composites as Solid Catalysts for the Alkenylation of C(sp3)-H Bonds Adjacent to a Heteroatom via Cross-Dehydrogenative Coupling
by Ha V. Le, Vy B. Nguyen, Hai H. Pham, Khoa D. Nguyen, Phuoc H. Ho, Philippe Trens and Francesco Di Renzo
Catalysts 2021, 11(10), 1252; https://doi.org/10.3390/catal11101252 - 18 Oct 2021
Cited by 2 | Viewed by 3025
Abstract
A series of mixed oxides of CuO, CeO2, and SiO2 were prepared by gel combustion and employed for the first time as efficient solid catalysts in a solvent-less liquid-phase cross-dehydrogenative coupling. The facile one-pot catalyst synthesis resulted in highly porous [...] Read more.
A series of mixed oxides of CuO, CeO2, and SiO2 were prepared by gel combustion and employed for the first time as efficient solid catalysts in a solvent-less liquid-phase cross-dehydrogenative coupling. The facile one-pot catalyst synthesis resulted in highly porous materials presenting large specific surface areas and strong metal–support interactions. The interaction with highly dispersed CeO2 enhanced the redox properties of the CuO species. The CuO-CeO2-SiO2 composites exhibited excellent catalytic performance for the selective coupling between 1,1-diphenylethylene and tetrahydrofuran with a yield up to 85% of 2-(2,2-diphenylvinyl)-tetrahydrofuran in the presence of di-tert-butyl peroxide (DTPB) and KI. Albeit both CuO and CeO2 species are proved to be responsible for the catalytic conversion, a great synergistic improvement in the catalytic activity was obtained by extended contact between the oxide phases by high porosity in comparison with the reactions using individual Cu or Ce catalysts. The activity of the composite catalyst was shown to be highly stable after five successive reaction cycles. Furthermore, the study scope was extended to the synthesis of different derivatives via composite-catalyzed coupling of C(sp2)-H with C(sp3-H) adjacent to a heteroatom. The good yields recorded proved the general validity of this composite for the cross-dehydrogenative coupling reaction rarely performed on solid catalysts. Full article
(This article belongs to the Special Issue Advances in Catalytic Coupling Reactions)
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12 pages, 3207 KiB  
Article
Hollow-Shell-Structured Mesoporous Silica-Supported Palladium Catalyst for an Efficient Suzuki-Miyaura Cross-Coupling Reaction
by Abdulelah Taher Ali Mohammed, Lijian Wang, Ronghua Jin, Guohua Liu and Chunxia Tan
Catalysts 2021, 11(5), 582; https://doi.org/10.3390/catal11050582 - 30 Apr 2021
Cited by 9 | Viewed by 3025
Abstract
The construction of a high stability heterogeneous catalyst for privileged common catalysis is a benefit in regard to reuse and separation. Herein, a palladium diphenylphosphine-based hollow-shell-structured mesoporous catalyst (HS@PdPPh2@MSN) was prepared by immobilizing bis((diphenylphosphino)ethyltriethoxysilane)palladium acetate onto the inner wall [...] Read more.
The construction of a high stability heterogeneous catalyst for privileged common catalysis is a benefit in regard to reuse and separation. Herein, a palladium diphenylphosphine-based hollow-shell-structured mesoporous catalyst (HS@PdPPh2@MSN) was prepared by immobilizing bis((diphenylphosphino)ethyltriethoxysilane)palladium acetate onto the inner wall of a mesoporous organicsilicane hollow shell, whose surface was protected by a –Si(Me)3 group. Electron microscopies confirmed its hollow-shell-structure, and structural analyses and characterizations revealed its well-defined single-site active species within the silicate network. As presented in this study, the newly constructed HS@PdPPh2@MSN enabled an efficient Suzuki-Miyaura cross-coupling reaction for varieties of substrates with up to 95% yield in mild conditions. Meanwhile, it could be reused at least five times with good activity, indicating its excellent stability and recyclability. Furthermore, the cost-effective and easily synthesized HS@PdPPh2@MSN made it a good candidate for employment in fine chemical engineering. Full article
(This article belongs to the Special Issue Advances in Catalytic Coupling Reactions)
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13 pages, 1992 KiB  
Article
Development of Facile and Simple Processes for the Heterogeneous Pd-Catalyzed Ligand-Free Continuous-Flow Suzuki–Miyaura Coupling
by Tsuyoshi Yamada, Jing Jiang, Naoya Ito, Kwihwan Park, Hayato Masuda, Chikara Furugen, Moeka Ishida, Seiya Ōtori and Hironao Sajiki
Catalysts 2020, 10(10), 1209; https://doi.org/10.3390/catal10101209 - 19 Oct 2020
Cited by 10 | Viewed by 3576
Abstract
The Suzuki–Miyaura coupling reaction is one of the most widely utilized C–C bond forming methods to create (hetero)biaryl scaffolds. The continuous-flow reaction using heterogeneous catalyst-packed cartridges is a practical and efficient synthetic method to replace batch-type reactions. A continuous-flow ligand-free Suzuki–Miyaura coupling reaction [...] Read more.
The Suzuki–Miyaura coupling reaction is one of the most widely utilized C–C bond forming methods to create (hetero)biaryl scaffolds. The continuous-flow reaction using heterogeneous catalyst-packed cartridges is a practical and efficient synthetic method to replace batch-type reactions. A continuous-flow ligand-free Suzuki–Miyaura coupling reaction of (hetero)aryl iodides, bromides, and chlorides with (hetero)aryl boronic acids was developed using cartridges packed with spherical resin (tertiary amine-based chelate resin: WA30)-supported palladium catalysts (7% Pd/WA30). The void space in the cartridge caused by the spherical catalyst structures enables the smooth flow of a homogeneously dissolved reaction solution that consists of a mixture of organic and aqueous solvents and is delivered by the use of a single syringe pump. Clogging or serious backpressure was not observed. Full article
(This article belongs to the Special Issue Advances in Catalytic Coupling Reactions)
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8 pages, 852 KiB  
Article
α, β-Alkynone Accelerated PPM Level Pd-Catalyzed Sonogashira Coupling Reaction
by Meng Guo, Zhen Wei, Jianming Yang, Zunyuan Xie and Weiqiang Zhang
Catalysts 2020, 10(3), 302; https://doi.org/10.3390/catal10030302 - 6 Mar 2020
Cited by 3 | Viewed by 2707
Abstract
In the palladium-catalyzed C−C coupling reaction, electron-rich phosphine ligands and a catalytic amount of catalyst loading are required in most cases. Herein, a bench-stable, easily modified and less toxic alkynone was utilized in palladium-catalyzed Sonogashira coupling to replace conventional phosphine ligands. With 1-(4-methoxyphenyl)-3-phenyl-2-yn-1-one [...] Read more.
In the palladium-catalyzed C−C coupling reaction, electron-rich phosphine ligands and a catalytic amount of catalyst loading are required in most cases. Herein, a bench-stable, easily modified and less toxic alkynone was utilized in palladium-catalyzed Sonogashira coupling to replace conventional phosphine ligands. With 1-(4-methoxyphenyl)-3-phenyl-2-yn-1-one (L2) as the ligand, catalyst loading was reduced to 5-10 ppm. In this newly developed catalytic system, a variety of (hetero)arene iodines and alkynes could be tolerated, resulting in good yields of the corresponding cross-coupling products. Full article
(This article belongs to the Special Issue Advances in Catalytic Coupling Reactions)
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Review

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50 pages, 30409 KiB  
Review
Recent Advancement of Ullmann Condensation Coupling Reaction in the Formation of Aryl-Oxygen (C-O) Bonding by Copper-Mediated Catalyst
by Choong Jian Fui, Mohd Sani Sarjadi, Shaheen M. Sarkar and Md Lutfor Rahman
Catalysts 2020, 10(10), 1103; https://doi.org/10.3390/catal10101103 - 24 Sep 2020
Cited by 27 | Viewed by 12252
Abstract
Transition metal-catalyzed chemical transformation of organic electrophiles and organometallic reagents belong to the most important cross coupling reaction in organic synthesis. The biaryl ether division is not only popular in natural products and synthetic pharmaceuticals but also widely found in many pesticides, polymers, [...] Read more.
Transition metal-catalyzed chemical transformation of organic electrophiles and organometallic reagents belong to the most important cross coupling reaction in organic synthesis. The biaryl ether division is not only popular in natural products and synthetic pharmaceuticals but also widely found in many pesticides, polymers, and ligands. Copper catalyst has received great attention owing to the low toxicity and low cost. However, traditional Ullmann-type couplings suffer from limited substrate scopes and harsh reaction conditions. The introduction of homogeneous copper catalyst with presence of bidentate ligands over the past two decades has totally changed this situation as these ligands enable the reaction promoted in mild condition. The reaction scope has also been greatly expanded, rendering this copper-based cross-coupling attractive for both academia and industry. In this review, we will highlight the latest progress in the development of useful homogeneous copper catalyst with presence of ligand and heterogeneous copper catalyst in Ullmann type C-O cross-coupling reaction. Additionally, the application of Ullmann type C-O cross coupling reaction will be discussed. Full article
(This article belongs to the Special Issue Advances in Catalytic Coupling Reactions)
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