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Nickel Complexes for Catalysis
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Nickel Complexes for Catalysis

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

Deadline for manuscript submissions: closed (29 February 2020) | Viewed by 18856

Special Issue Editor

Prof. Dr. Kouki Matsubara

E-Mail
Guest Editor
Fukuoka University, 8-19-1 Nanakuma, Fukuoka 814-0180, Japan
Interests: organometallic chemistry; homogeneous catalysis; first-row transition metals; N-heterocyclic carbenes; mechanistic studies

Special Issue Information

Dear Colleagues,

The chemistry of nickel complexes and their use in homogeneous catalysis have been under development for decades, along with those of palladium. Originally, the key player in the field was palladium, and nickel rarely attracted the community’s attention to its specific features. However, the increasing significance of first-row transition metal catalysis and the development of catalysts for important reactions, such as olefin polymerization, allylic substitution, cross coupling or oxidative coupling of unsaturated bonds; has led to the rise of nickel chemistry. Multiple novel ligands have been designed, and many new complexes are being developed and their catalytic features studied, denoting the unique characteristics that differentiate nickel from palladium.

This Special Issue aims to highlight the current chemistry of nickel complexes and nickel-based catalysis. Researchers working on the basic study of nickel chemistry as well as on the development of nickel complexes for catalysis, catalytic applications in organic transformations, and mechanistic studies are invited to contribute original research articles, as well as reviews and perspectives to be included in this Special Issue of Molecules.

Prof. Kouki Matsubara
Guest Editor

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. 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

  • Nickel catalysts
  • Homogeneous reactions
  • Organic transformation
  • Asymmetric synthesis
  • Reaction mechanism
  • DFT calculation
  • Ligand design
  • Olefin polymerization
  • C-H activation
  • Cross coupling

Published Papers (4 papers)

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Research

11 pages, 1638 KiB  
Communication
Fluorine-Substituted Arylphosphine for an NHC-Ni(I) System, Air-Stable in a Solid State but Catalytically Active in Solution
by Kouki Matsubara, Takahiro Fujii, Rion Hosokawa, Takahiro Inatomi, Yuji Yamada and Yuji Koga
Molecules 2019, 24(18), 3222; https://doi.org/10.3390/molecules24183222 - 04 Sep 2019
Cited by 4 | Viewed by 2831
Abstract
Monovalent NHC-nickel complexes bearing triarylphosphine, in which fluorine is incorporated onto the aryl groups, have been synthesized. Tris(3,5-di(trifluoromethyl)-phenyl)phosphine efficiently gave a monovalent nickel bromide complex, whose structure was determined by X-ray diffraction analysis for the first time. In the solid state, the Ni(I) [...] Read more.
Monovalent NHC-nickel complexes bearing triarylphosphine, in which fluorine is incorporated onto the aryl groups, have been synthesized. Tris(3,5-di(trifluoromethyl)-phenyl)phosphine efficiently gave a monovalent nickel bromide complex, whose structure was determined by X-ray diffraction analysis for the first time. In the solid state, the Ni(I) complex was less susceptible to oxidation in air than the triphenylphosphine complex, indicating greatly improved solid-state stability. In contrast, the Ni(I) complex in solution can easily liberate the phosphine, high catalytic activity toward the Kumada–Tamao–Corriu coupling of aryl bromides. Full article
(This article belongs to the Special Issue Nickel Complexes for Catalysis)
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12 pages, 5683 KiB  
Article
Cross-Coupling Reaction of Allylic Ethers with Aryl Grignard Reagents Catalyzed by a Nickel Pincer Complex
by Toru Hashimoto, Kei Funatsu, Atsufumi Ohtani, Erika Asano and Yoshitaka Yamaguchi
Molecules 2019, 24(12), 2296; https://doi.org/10.3390/molecules24122296 - 21 Jun 2019
Cited by 9 | Viewed by 4143
Abstract
A cross-coupling reaction of allylic aryl ethers with arylmagnesium reagents was investigated using β-aminoketonato- and β-diketiminato-based pincer-type nickel(II) complexes as catalysts. An β-aminoketonato nickel(II) complex bearing a diphenylphosphino group as a third donor effectively catalyzed the reaction to afford the target cross-coupled products, [...] Read more.
A cross-coupling reaction of allylic aryl ethers with arylmagnesium reagents was investigated using β-aminoketonato- and β-diketiminato-based pincer-type nickel(II) complexes as catalysts. An β-aminoketonato nickel(II) complex bearing a diphenylphosphino group as a third donor effectively catalyzed the reaction to afford the target cross-coupled products, allylbenzene derivatives, in high yield. The regioselective reaction of a variety of substituted cinnamyl ethers proceeded to give the corresponding linear products. In contrast, α- and γ-alkyl substituted allylic ethers afforded a mixture of the linear and branched products. These results indicated that the coupling reaction proceeded via a π-allyl nickel intermediate. Full article
(This article belongs to the Special Issue Nickel Complexes for Catalysis)
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11 pages, 4561 KiB  
Article
Nickel-Catalyzed Decarbonylative Stannylation of Acyl Fluorides under Ligand-Free Conditions
by Xiu Wang, Zhenhua Wang, Li Liu, Yuya Asanuma and Yasushi Nishihara
Molecules 2019, 24(9), 1671; https://doi.org/10.3390/molecules24091671 - 28 Apr 2019
Cited by 32 | Viewed by 4512
Abstract
Nickel-catalyzed decarbonylative stannylation of acyl fluorides under ligand-free conditions was disclosed. A variety of aromatic acyl fluorides are capable of reacting with silylstannanes in the presence of cesium fluoride. A one-pot decarbonylative stannylation/Migita-Kosugi-Stille reaction of benzoyl fluoride, giving rise to the direct formation [...] Read more.
Nickel-catalyzed decarbonylative stannylation of acyl fluorides under ligand-free conditions was disclosed. A variety of aromatic acyl fluorides are capable of reacting with silylstannanes in the presence of cesium fluoride. A one-pot decarbonylative stannylation/Migita-Kosugi-Stille reaction of benzoyl fluoride, giving rise to the direct formation of the corresponding cross-coupled products, further demonstrated the synthetic utility of the present method. This newly developed methodology with a good functional-group compatibility via C–F bond cleavage and C–Sn bond formation under nickel catalysis opens a new area for the functionalization of acyl fluorides in terms of carbon-heteroatom bond formation. Full article
(This article belongs to the Special Issue Nickel Complexes for Catalysis)
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11 pages, 5021 KiB  
Communication
Ni/Co-Catalyzed Homo-Coupling of Alkyl Tosylates
by Kimihiro Komeyama, Ryusuke Tsunemitsu, Takuya Michiyuki, Hiroto Yoshida and Itaru Osaka
Molecules 2019, 24(8), 1458; https://doi.org/10.3390/molecules24081458 - 12 Apr 2019
Cited by 13 | Viewed by 5335
Abstract
A direct reductive homo-coupling of alkyl tosylates has been developed by employing a combination of nickel and nucleophilic cobalt catalysts. A single-electron-transfer-type oxidative addition is a pivotal process in the well-established nickel-catalyzed coupling of alkyl halides. However, the method cannot be applied to [...] Read more.
A direct reductive homo-coupling of alkyl tosylates has been developed by employing a combination of nickel and nucleophilic cobalt catalysts. A single-electron-transfer-type oxidative addition is a pivotal process in the well-established nickel-catalyzed coupling of alkyl halides. However, the method cannot be applied to the homo-coupling of ubiquitous alkyl tosylates due to the high-lying σ*(C–O) orbital of the tosylates. This paper describes a Ni/Co-catalyzed protocol for the activation of alkyl tosylates on the construction of alkyl dimers under mild conditions. Full article
(This article belongs to the Special Issue Nickel Complexes for Catalysis)
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