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Transition Metal Complexes as Catalysts in Organic Chemistry
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Transition Metal Complexes as Catalysts in Organic Chemistry

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 October 2020) | Viewed by 43218

Special Issue Editor

Dr. Dmytro Nesterov

E-Mail Website1 Website2
Guest Editor
Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049-001 Lisboa, Portugal
Interests: homogeneous catalysis; selective catalysis; oxidative transformations; C–H activation; catalysis by poly- and hetero-metallic complexes; reaction mechanisms; synthesis of coordination compounds

Special Issue Information

Dear Colleagues,

The coordination compounds of transition metals occupy a special place among the catalysts in organic chemistry because of their pronounced activity and their variety of properties. The catalytic features of transition metal complexes are under the strong influence of their ligands, which, in this way, become a useful tool to control the properties of the catalytic system. The design of the structure of a coordination compound (catalyst) is of crucial importance for its catalytic applications. Despite the great progress in understanding the structure–properties correlations, as well as the development of numerous synthetic processes, the catalytic parameters of many reactions are far from perfect, especially in the field of fine chemistry (such as asymmetric C–H functionalization, activation of small molecules, and others).

This Special Issue is focused on the recent advances in the catalytic applications of transition metal complexes towards the organic transformations, including C–H activation, C–C coupling, and so on. This covers the investigation of the fundamental processes and reaction mechanisms, as well as the development of novel synthetic protocols involving transition metal complexes as catalysts.

Dr. Dmytro Nesterov
Guest Editor

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Keywords

  • Homogeneous catalysis
  • Complexes of transition metals
  • Polynuclear complexes and heterometallic complexes
  • Reaction intermediates
  • Catalytic mechanisms
  • Organic synthesis

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Published Papers (6 papers)

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Research

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13 pages, 2488 KiB  
Article
One-Pot Synthesis of B-Aryl Carboranes with Sensitive Functional Groups Using Sequential Cobalt- and Palladium-Catalyzed Reactions
by Sergey A. Anufriev, Akim V. Shmal’ko, Kyrill Yu. Suponitsky and Igor B. Sivaev
Catalysts 2020, 10(11), 1348; https://doi.org/10.3390/catal10111348 - 19 Nov 2020
Cited by 5 | Viewed by 2864
Abstract
The simple and efficient method was developed for the one-pot synthesis of B-substituted aryl derivatives of ortho-carborane with functional groups sensitive to organolithium and organomagnesium reagents using 9-iodo-ortho-carborane and generated in situ organozinc compounds. The method proposed was used [...] Read more.
The simple and efficient method was developed for the one-pot synthesis of B-substituted aryl derivatives of ortho-carborane with functional groups sensitive to organolithium and organomagnesium reagents using 9-iodo-ortho-carborane and generated in situ organozinc compounds. The method proposed was used to prepare a series of 9-aryl-ortho-carboranes, including those containing nitrile and ester groups, 9-RC6H4-1,2-C2B10H11 (R = p-Me, p-NMe2, p-OCH2OMe, o-OMe, p-OMe, o-CN, p-CN, o-COOEt, m-COOEt, and p-COOEt). It was demonstrated that the same approach can be used for synthesis of diaryl derivatives of ortho-carborane 9,12-(RC6H4)2-1,2-C2B10H10 (R = H, p-Me). The solid-state structures of 9-RC6H4-1,2-C2B10H11 (R = p-NMe2, p-OCH2OMe, o-OMe, o-CN, p-CN, m-COOEt, and p-COOEt) and 9,12-(p-MeC6H4)2-1,2-C2B10H10 were determined by single crystal X-ray diffraction. Full article
(This article belongs to the Special Issue Transition Metal Complexes as Catalysts in Organic Chemistry)
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21 pages, 3082 KiB  
Article
(±)-trans-1,2-Cyclohexanediamine-Based Bis(NHC) Ligand for Cu-Catalyzed Asymmetric Conjugate Addition Reaction
by Azusa Ishibashi, Shun Kamihigashi, Yuuki Iwai and Satoshi Sakaguchi
Catalysts 2019, 9(9), 780; https://doi.org/10.3390/catal9090780 - 19 Sep 2019
Cited by 7 | Viewed by 3797
Abstract
Bis(NHC) ligand precursors, L1, based on trans-1,2-diaminocyclohexane were designed and synthesized. To introduce chirality at the hydroxyamide side arm on the NHC of L1, a chiral β-amino alcohol, such as enantiopure leucinol, was used. Cu-catalyzed asymmetric conjugate addition reactions [...] Read more.
Bis(NHC) ligand precursors, L1, based on trans-1,2-diaminocyclohexane were designed and synthesized. To introduce chirality at the hydroxyamide side arm on the NHC of L1, a chiral β-amino alcohol, such as enantiopure leucinol, was used. Cu-catalyzed asymmetric conjugate addition reactions of cyclic and acyclic enones with Et2Zn were selected to evaluate the performance of L1 as a chiral ligand. For the reaction of cyclic enone, a combination of [bis(trimethylsilyl)acetylene]-(hexafluoroacetylacetonato)copper(I) (Cu(hfacac)(btmsa)) with a (±)-trans-1,2-cyclohexanediamine-based bis(NHC) ligand precursor, (rac; S,S)-L1, which was prepared from (S)-leucinol, was the most effective. Thus, treating 2-cyclohexen-1-one (3) with Et2Zn in the presence of catalytic amounts of Cu(hfacac)(btmsa) and (rac; S,S)-L1 afforded (R)-3-ethylcyclohexanone ((R)-4) with 97% ee. Similarly, use of (rac; R,R)-L1, which was prepared from (R)-leucinol, produced (S)-4 with 97% ee. Conversely, for the asymmetric 1,4-addition reaction of the acyclic enone, optically pure (−)-trans-1,2-cyclohexanediamine-based bis(NHC) ligand precursor, (R,R; S,S)-L1, worked efficiently. For example, 3-nonen-2-one (5) was reacted with Et2Zn using the CuOAc/(R,R; S,S)-L1 catalytic system to afford (R)-4-ethylnonan-2-one ((R)-6) with 90% ee. Furthermore, initially changing the counterion of the Cu precatalyst between an OAc and a ClO4 ligand on the metal reversed the facial selectivity of the approach of the substrates. Thus, the conjugate addition reaction of 5 with Et2Zn using the Cu(ClO4)2/(R,R; S,S)-L1 catalytic system, afforded (S)-6 with 75% ee. Full article
(This article belongs to the Special Issue Transition Metal Complexes as Catalysts in Organic Chemistry)
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18 pages, 4250 KiB  
Article
Heterogeneous Bimetallic Cu–Ni Nanoparticle-Supported Catalysts in the Selective Oxidation of Benzyl Alcohol to Benzaldehyde
by Lili Liu, Xiaojing Zhou, Li Liu, Shuai Jiang, Yingjie Li, Luxia Guo, Shijuan Yan and Xishi Tai
Catalysts 2019, 9(6), 538; https://doi.org/10.3390/catal9060538 - 17 Jun 2019
Cited by 22 | Viewed by 4616
Abstract
Three bimetallic Cu–Ni nanoparticle-supported catalysts were synthesized by co-immobilization followed by H2 reduction. A chromium(III) terephthalate metal organic framework (MIL-101), titanium dioxide (TiO2), and carbon (C) with different properties (acidity and Brunauer–Emmett–Teller surface area) were selected as supports for studying [...] Read more.
Three bimetallic Cu–Ni nanoparticle-supported catalysts were synthesized by co-immobilization followed by H2 reduction. A chromium(III) terephthalate metal organic framework (MIL-101), titanium dioxide (TiO2), and carbon (C) with different properties (acidity and Brunauer–Emmett–Teller surface area) were selected as supports for studying the effect of the support nature on the catalytic activity and selectivity in the oxidation of benzyl alcohol. The physicochemical properties of the Cu–Ni-supported catalysts were characterized by XRD, NH3-TPD, nitrogen adsorption/desorption, TEM, EDS, XPS, and ICP-OES. Bimetallic Cu–Ni nanoparticles were highly dispersed on the support. The catalytic activities of CuNi/MIL-101, CuNi/TiO2, and CuNi/C were tested in the selective oxidation of benzyl alcohol to benzaldehyde in the presence of molecular oxygen under mild reaction conditions. The highest benzaldehyde yields were achieved with CuNi/TiO2, CuNi/MIL-101, and CuNi/C catalysts at 100 °C within 4 h under 5, 3, and 3 bar of O2, respectively. The bimetallic Cu–Ni-supported catalysts possessed two types of catalytic active sites: acid sites and bimetallic Cu–Ni nanoparticles. The CuNi/MIL-101 catalyst possessed a high number of acid sites and exhibited high yield during selective benzyl alcohol oxidation to benzaldehyde. Importantly, the catalysts exhibited a high functional group (electron-donating and electron-withdrawing groups) tolerance. Cu–Ni-supported catalysts with an Cu:Ni mole ratio of 1:1 exhibited the highest yield of 47% for the selective oxidation of benzyl alcohol to benzaldehyde. Reusability and leaching experiment results exhibited that CuNi/MIL-101 showed better stability than CuNi/TiO2 and CuNi/C catalysts due to the large porous cavities of MIL-101 support; these cavities can be used to trap bimetallic Cu–Ni nanoparticles and inhibit nanoparticle leaching. Full article
(This article belongs to the Special Issue Transition Metal Complexes as Catalysts in Organic Chemistry)
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16 pages, 3735 KiB  
Article
Tetracopper(II) Cores Driven by an Unexplored Trifunctional Aminoalcohol Sulfonic Acid for Mild Catalytic C–H Functionalization of Alkanes
by Inês F. M. Costa, Marina V. Kirillova, Vânia André, Tiago A. Fernandes and Alexander M. Kirillov
Catalysts 2019, 9(4), 321; https://doi.org/10.3390/catal9040321 - 1 Apr 2019
Cited by 7 | Viewed by 4772
Abstract
Three new tetracopper(II) coordination compounds were easily generated from Cu(NO3)2, a trifunctional aminoalcohol sulfonic acid (H3bes, N,N-bis(2-hydroxyethyl)-2-aminoethanesulfonic acid) as a principal building block, and a benzene carboxylic acid as a supporting ligand (i.e., benzoic [...] Read more.
Three new tetracopper(II) coordination compounds were easily generated from Cu(NO3)2, a trifunctional aminoalcohol sulfonic acid (H3bes, N,N-bis(2-hydroxyethyl)-2-aminoethanesulfonic acid) as a principal building block, and a benzene carboxylic acid as a supporting ligand (i.e., benzoic (Hba), 4-hydroxybenzoic (Hfba), or 3-hydroxybenzoic (Hthba) acid). The obtained microcrystalline products, [Cu4(µ-Hbes)3(µ-H2bes)(µ-L)]·2H2O (L = ba− (1), fhba− (2), and thba− (3)), were fully characterized by FTIR (Fourier-transform infrared spectroscopy), elemental analysis, ESI-MS (Electrospray Ionisation Mass Spectrometry), and single-crystal X-ray diffraction methods. Compounds 1–3 were applied as effective homogeneous catalysts in the oxidative C−H functionalization of alkanes (cycloalkanes and propane). Two different model reactions were explored: (1) mild oxidation of alkanes with hydrogen peroxide to give alcohols and ketones, and (2) mild carboxylation of alkanes with carbon monoxide, water, and potassium peroxodisulfate to give carboxylic acids. For these reactions, effects of different parameters, as well as mechanistic and selectivity characteristics, were studied. Full article
(This article belongs to the Special Issue Transition Metal Complexes as Catalysts in Organic Chemistry)
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10 pages, 5550 KiB  
Communication
Aerobic Epoxidation of Low-Molecular-Weight and Polymeric Olefins by a Supramolecular Manganese Porphyrin Catalyst
by Ivan Bernar, Floris P.J.T. Rutjes, Johannes A.A.W. Elemans and Roeland J.M. Nolte
Catalysts 2019, 9(2), 195; https://doi.org/10.3390/catal9020195 - 21 Feb 2019
Cited by 25 | Viewed by 5008
Abstract
We report on the highly efficient epoxidation of low-molecular-weight and polymeric olefins catalyzed by a supramolecular manganese porphyrin complex using molecular oxygen as an oxidant and an aldehyde as a co-reductant. At ambient temperature and under optimized reaction conditions, the catalyst showed high [...] Read more.
We report on the highly efficient epoxidation of low-molecular-weight and polymeric olefins catalyzed by a supramolecular manganese porphyrin complex using molecular oxygen as an oxidant and an aldehyde as a co-reductant. At ambient temperature and under optimized reaction conditions, the catalyst showed high activity and stereoselectivity. The efficiency of the supramolecular manganese porphyrin was higher than that of a reference porphyrin catalyst, possibly because it was more stable under the applied reaction conditions. Mechanistic studies suggest that a manganese oxo porphyrin complex may be an intermediate in the epoxidation reaction. Full article
(This article belongs to the Special Issue Transition Metal Complexes as Catalysts in Organic Chemistry)
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Review

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48 pages, 15544 KiB  
Review
Palladium and Copper Catalyzed Sonogashira cross Coupling an Excellent Methodology for C-C Bond Formation over 17 Years: A Review
by Iram Kanwal, Aqsa Mujahid, Nasir Rasool, Komal Rizwan, Ayesha Malik, Gulraiz Ahmad, Syed Adnan Ali Shah, Umer Rashid and Nadiah Mad Nasir
Catalysts 2020, 10(4), 443; https://doi.org/10.3390/catal10040443 - 20 Apr 2020
Cited by 104 | Viewed by 18471
Abstract
Sonogashira coupling involves coupling of vinyl/aryl halides with terminal acetylenes catalyzed by transition metals, especially palladium and copper. This is a well known reaction in organic synthesis and plays a role in sp2-sp C-C bond formations. This cross coupling was used [...] Read more.
Sonogashira coupling involves coupling of vinyl/aryl halides with terminal acetylenes catalyzed by transition metals, especially palladium and copper. This is a well known reaction in organic synthesis and plays a role in sp2-sp C-C bond formations. This cross coupling was used in synthesis of natural products, biologically active molecules, heterocycles, dendrimers, conjugated polymers and organic complexes. This review paper focuses on developments in the palladium and copper catalyzed Sonogashira cross coupling achieved in recent years concerning substrates, different catalyst systems and reaction conditions. Full article
(This article belongs to the Special Issue Transition Metal Complexes as Catalysts in Organic Chemistry)
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