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Catalysts
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Recent Advances in Organometallic Chemistry and Catalysis
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Recent Advances in Organometallic Chemistry and Catalysis

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 (31 December 2020) | Viewed by 33589

Special Issue Editor

Prof. Dr. Victorio Cadierno

E-Mail Website
Guest Editor
Department of Organic and Inorganic Chemistry, University of Oviedo, Julián Clavería 8, 33006 Oviedo, Spain
Interests: homogeneous catalysis; aqueous catalysis; green chemistry; organometallic and coordination chemistry; alternative reaction media; organic synthesis
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Organometallic compounds have had a tremendous impact on modern organic synthesis and are nowadays commonly employed as catalysts for the production of fine chemicals, pharmaceuticals and materials, such as polymers. In addition, organometallic catalysis gives the opportunity to assemble organic molecules in a highly efficient and selective manner that cannot be envisioned otherwise, and can be applied in the development of improved sustainable chemical transformations.

This special issue of Catalysts intends to cover recent developments in the application of organometallic compounds in catalytic organic synthesis, including mechanistic studies. Submissions are very welcome in the form of original research papers or short reviews that reflect the state of research in the field.

Prof. Dr. Victorio Cadierno
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. Catalysts is an international peer-reviewed open access monthly journal published by MDPI.

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Published Papers (8 papers)

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Editorial

Jump to: Research, Review

4 pages, 179 KiB  
Editorial
Recent Advances in Organometallic Chemistry and Catalysis
by Victorio Cadierno
Catalysts 2021, 11(5), 646; https://doi.org/10.3390/catal11050646 - 19 May 2021
Cited by 5 | Viewed by 4566
Abstract
The use of organometallic compounds in organic chemistry is one of the cornerstones of the modern synthetic methodology for the activation and generation of new bonds in a molecule [...] Full article
(This article belongs to the Special Issue Recent Advances in Organometallic Chemistry and Catalysis)

Research

Jump to: Editorial, Review

9 pages, 2898 KiB  
Communication
Indium-Catalyzed Cycloisomerization of 1,6-Cyclohexenylalkynes
by Vincent Davenel, Chloé Puteaux, Christian Nisole, Fabien Fontaine-Vive, Jean-Marie Fourquez and Véronique Michelet
Catalysts 2021, 11(5), 546; https://doi.org/10.3390/catal11050546 - 24 Apr 2021
Cited by 6 | Viewed by 2497
Abstract
Efficient four- and five-step routes to access functionalized bicyclo[3.2.1]oct-2-ene and bicyclo[3.3.1]nonadiene via indium-mediated cycloisomerization of 1,6-enynes has been developed. This atom-economical catalytic process was optimized and relied on the efficiency of InCl3 leading to the preparation of functionalized bicyclic adducts in up [...] Read more.
Efficient four- and five-step routes to access functionalized bicyclo[3.2.1]oct-2-ene and bicyclo[3.3.1]nonadiene via indium-mediated cycloisomerization of 1,6-enynes has been developed. This atom-economical catalytic process was optimized and relied on the efficiency of InCl3 leading to the preparation of functionalized bicyclic adducts in up to 99% isolated yield. The cyclization occurred on two different processes (5-exo versus 6-endo pathway) and were influenced by the substitution of the alkynyl moiety. The exo process was favored for non-substituted alkynes whereas the endo pathway was generally observed for substituted alkynes. Then, the presence of electron-withdrawing groups on the aryl substituted alkyne increased the ratio of the exo isomer. DFT calculations were performed on stability of intermediates and corroborated the intervention of InCl3. Full article
(This article belongs to the Special Issue Recent Advances in Organometallic Chemistry and Catalysis)
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17 pages, 2271 KiB  
Article
Hydrogenation of α,β-Unsaturated Carbonyl Compounds over Covalently Heterogenized Ru(II) Diphosphine Complexes on AlPO4-Sepiolite Supports
by Verónica Caballero, Rafael Estevez, Diego Luna, Felipa M. Bautista, Antonio A. Romero, Laura Aguado-Deblas, Jesús Hidalgo-Carrillo and Isabel Romero
Catalysts 2021, 11(2), 289; https://doi.org/10.3390/catal11020289 - 22 Feb 2021
Cited by 1 | Viewed by 2792
Abstract
In this work, the covalent immobilization of two ruthenium(II) complexes, i.e., [RuIICl (bpea){(S)(-)(BINAP)}](BF4), 1, and [RuIICl(bpea)(DPPE)](BF4), 2, where BINAP = 2,2’-bis(diphenylphosphino)-1,1’-binaphthyl and DPPE = 1,2-bis(diphenylphosphino)ethane, have been obtained (AlPO4-Sepiolite@1 and AlPO [...] Read more.
In this work, the covalent immobilization of two ruthenium(II) complexes, i.e., [RuIICl (bpea){(S)(-)(BINAP)}](BF4), 1, and [RuIICl(bpea)(DPPE)](BF4), 2, where BINAP = 2,2’-bis(diphenylphosphino)-1,1’-binaphthyl and DPPE = 1,2-bis(diphenylphosphino)ethane, have been obtained (AlPO4-Sepiolite@1 and AlPO4-Sepiolite@2) by using a N-tridentate ligand N,N-bis-(2-pyridylmethyl)ethylamine (bpea), linked to an amorphous AlPO4-Sepiolite (20/80) inorganic support. This AlPO4-sepiolite support is able to immobilize the double amount of ruthenium complex (1.65%) than the amorphous AlPO4 (0.89%). Both heterogenized complexes have been assessed as catalysts in the liquid phase hydrogenation of several substrates with carbonyl and/or olefinic double bonds using methanol as solvent, attaining good catalytic activity and high enantioselectivity (99%). The highest Turn Over Number (TON) value (748.6) was obtained over the [RuII Cl (bpea)(DPPE)](BF4) 2 catalyst, although the [RuIICl(bpea){(S)(-)(BINAP)}](BF4) 1 exhibits better reusability. In fact, the [RuIICl(bpea){(S)(-)(BINAP)}](BF4) immobilized on AlPO4-Sepiolite maintained the activity throughout 14 successive runs. Furthermore, some findings on hydrogenation mechanisms of the α,β-unsaturated carbonyl compounds over Ru catalysts have been also obtained. Full article
(This article belongs to the Special Issue Recent Advances in Organometallic Chemistry and Catalysis)
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7 pages, 1837 KiB  
Article
Adipic Acid Route: Oxidation of Cyclohexene vs. Cyclohexane
by Ana P. C. Ribeiro, Elisa Spada, Roberta Bertani and Luísa M. D. R. S. Martins
Catalysts 2020, 10(12), 1443; https://doi.org/10.3390/catal10121443 - 10 Dec 2020
Cited by 15 | Viewed by 5515
Abstract
A cleaner alternative to the current inefficient oxidation of cyclohexane to adipic acid is presented. Direct oxidation of neat cyclohexene by aq. hydrogen peroxide to adipic acid is selectively achieved in good yield (46%), in the presence of the recyclable C-homoscorpionate iron(II) complex [...] Read more.
A cleaner alternative to the current inefficient oxidation of cyclohexane to adipic acid is presented. Direct oxidation of neat cyclohexene by aq. hydrogen peroxide to adipic acid is selectively achieved in good yield (46%), in the presence of the recyclable C-homoscorpionate iron(II) complex [FeCl2{κ3-HC(pz)3}] (pz = pyrazol-1-yl) and microwave irradiation, by a nitrous oxide-free protocol. Full article
(This article belongs to the Special Issue Recent Advances in Organometallic Chemistry and Catalysis)
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11 pages, 1139 KiB  
Article
Biological Activities of NHC–Pd(II) Complexes Based on Benzimidazolylidene N-heterocyclic Carbene (NHC) Ligands Bearing Aryl Substituents
by Ibrahim Al Nasr, Nedra Touj, Waleed Koko, Tariq Khan, Ismail Özdemir, Sedat Yaşar and Naceur Hamdi
Catalysts 2020, 10(10), 1190; https://doi.org/10.3390/catal10101190 - 15 Oct 2020
Cited by 23 | Viewed by 3619
Abstract
N-heterocyclic carbene (NHC) precursors (2a–i), their pyridine-enhanced precatalyst preparation stabilization and initiation (PEPPSI)-themed palladium N-heterocyclic carbene complexes (3a–i) and palladium N-heterocyclic triphenylphosphines complexes (4a–i) were synthesized and characterized by elemental analysis and 1H NMR, 13C [...] Read more.
N-heterocyclic carbene (NHC) precursors (2a–i), their pyridine-enhanced precatalyst preparation stabilization and initiation (PEPPSI)-themed palladium N-heterocyclic carbene complexes (3a–i) and palladium N-heterocyclic triphenylphosphines complexes (4a–i) were synthesized and characterized by elemental analysis and 1H NMR, 13C NMR, IR, and LC–MS spectroscopic techniques. The (NHC)Pd(II) complexes 3–4 were tested against MCF7 and MDA-MB-231 cancer cells, Escherichia coli, methicillin-resistant Staphylococcus aureus (MRSA), Candida albicans microorganisms, Leishmania major promastigotes and amastigotes, Toxoplasma gondii parasites, and Vero cells in vitro. The biological assays indicated that all compounds are highly active against cancer cells, with an IC50 < 1.5 µg mL−1. Eight compounds proved antibacterial and antileishmanial activities, while only three compounds had strong antifungal activities against C. albicans. In our conclusion, compounds 3 (b, f, g, and h) and 4b are the most suitable drug candidates for anticancer, antimicrobial, and antiparasitical. Full article
(This article belongs to the Special Issue Recent Advances in Organometallic Chemistry and Catalysis)
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Scheme 1

20 pages, 9349 KiB  
Article
Specialized Olefin Metathesis Catalysts Featuring Unsymmetrical N-Heterocyclic Carbene Ligands Bearing N-(Fluoren-9-yl) Arm
by Phillip I. Jolly, Anna Marczyk, Paweł Małecki, Damian Trzybiński, Krzysztof Woźniak, Anna Kajetanowicz and Karol Grela
Catalysts 2020, 10(6), 599; https://doi.org/10.3390/catal10060599 - 27 May 2020
Cited by 8 | Viewed by 3063
Abstract
Beneficial structural motifs from two known state-of-the-art olefin metathesis catalysts types, bearing unsymmetrical N-heterocyclic carbenes (uNHCs), were combined into a new hybridized design thereby translating the complementary beneficial reactivity demonstrated by their ‘parent’ complexes to the new N-fluorene derived olefin metathesis [...] Read more.
Beneficial structural motifs from two known state-of-the-art olefin metathesis catalysts types, bearing unsymmetrical N-heterocyclic carbenes (uNHCs), were combined into a new hybridized design thereby translating the complementary beneficial reactivity demonstrated by their ‘parent’ complexes to the new N-fluorene derived olefin metathesis catalysts. Two chelating 2-iso-propoxy-benzylidene (Hoveyda-type) and two 3-phenyl-1H-inden-1-ylidene (indenylidene-type) complexes were successfully prepared by in situ generation of either the N′-mesityl (Mes) or N′-diisopropylphenyl (Dipp) derived uNHCs taking advantage of the thermal decomposition of the corresponding 2-(penta-fluorophenyl)-imidazolidines (NHC adducts). The new fluorene-derived catalysts mediate challenging olefin metathesis processes, such as α-olefin self-metathesis, with high selectivity and conversion. Full article
(This article belongs to the Special Issue Recent Advances in Organometallic Chemistry and Catalysis)
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Review

Jump to: Editorial, Research

36 pages, 12381 KiB  
Review
Gold-Catalyzed Addition of Carboxylic Acids to Alkynes and Allenes: Valuable Tools for Organic Synthesis
by Victorio Cadierno
Catalysts 2020, 10(10), 1206; https://doi.org/10.3390/catal10101206 - 18 Oct 2020
Cited by 24 | Viewed by 5059
Abstract
In this contribution, the application of gold-based catalysts in the hydrofunctionalization reactions of alkynes and allenes with carboxylic acids is comprehensively reviewed. Both intra- and intermolecular processes, leading respectively to lactones and linear unsaturated esters, are covered. In addition, cascade transformations involving the [...] Read more.
In this contribution, the application of gold-based catalysts in the hydrofunctionalization reactions of alkynes and allenes with carboxylic acids is comprehensively reviewed. Both intra- and intermolecular processes, leading respectively to lactones and linear unsaturated esters, are covered. In addition, cascade transformations involving the initial cycloisomerization of an alkynoic acid are also discussed. Full article
(This article belongs to the Special Issue Recent Advances in Organometallic Chemistry and Catalysis)
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22 pages, 6370 KiB  
Review
Metal-Catalyzed Synthesis and Transformations of β-Haloenol Esters
by Victorio Cadierno
Catalysts 2020, 10(4), 399; https://doi.org/10.3390/catal10040399 - 4 Apr 2020
Cited by 5 | Viewed by 3192
Abstract
In the last years there has been an increasing interest in the search for protocols to obtain β-haloenol esters in an efficient and selective manner as they are versatile building blocks in synthetic organic chemistry. In this article, metal-catalyzed transformations allowing the [...] Read more.
In the last years there has been an increasing interest in the search for protocols to obtain β-haloenol esters in an efficient and selective manner as they are versatile building blocks in synthetic organic chemistry. In this article, metal-catalyzed transformations allowing the access to both acyclic and cyclic (i.e., haloenol lactones) β-haloenol esters are reviewed. Metal-catalyzed reactions in which these molecules participate as substrates are also discussed. Full article
(This article belongs to the Special Issue Recent Advances in Organometallic Chemistry and Catalysis)
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