Special Issue "Catalysis in Heterocyclic and Organometallic Synthesis"

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: 30 November 2020.

Special Issue Editor

Prof. Dr. Antal Csámpai
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Guest Editor
Institute of Chemistry, Faculty of Science, Eötvös Loránd University (ELTE), Pázmány Péter sétány 1/A, 1117 Budapest, Hungary
Interests: Heterocyclic chemistry; Organometallic chemistry of transition metals; NMR spectroscopy; Stereochemistry; Molecular modelling; Antiproliferative compounds; Cross coupling reactions; Organocatalysis
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Special Issue Information

Dear Colleagues,

In the last decades, diverse methods of catalysis, including transition metal catalysis, organocatalysis, their homogenous and heterogenous versions as well as biocatalysis, witnessed an extremely rapid development in a variety of chemical transformations utilised in chemical, fuel, pharmaceutical and agricultural industries to afford a wide range of products having impact on daily life. As a results of intensive research a number of well-established concepts and tools are now available to get a deeper insight into the mechanisms of catalytic reactions allowing to develop more and more sophisticated catalytic systems and conditions capable of governing the elementary steps of a multistep transformation to proceed via a rationally designed pathway. Although in the chemistry of heterocyclic and organometallic compounds, representing two large and partly overlapping domains of chemical research, the most efficient, robust and often environmentally benign synthetic strategies are based on catalysis, there is a constant need to develop further superior systems of higher catalytic activity and specificity and to elaborate catalytic versions of extensively used stoichiometric organic syntheses with particular regards to asymmetric transformations.

Prof. Dr. Antal Csámpai
Guest Editor

Manuscript Submission Information

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Keywords

  • Heterocyclic synthesis
  • Synthesis of organometallics
  • Metal catalysis
  • Organocatalysis
  • Biocatalysis
  • Chemoselective transformations
  • Asymmetric synthesis
  • Catalytic annulation reactions
  • Enantioselective syntheses
  • Reaction mechanism

Published Papers (5 papers)

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Research

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Open AccessArticle
Redox Isomerization of Allylic Alcohols Catalyzed by New Water-Soluble Rh(I)-N-Heterocyclic Carbene Complexes
Catalysts 2020, 10(11), 1361; https://doi.org/10.3390/catal10111361 - 23 Nov 2020
Abstract
New water-soluble, N-heterocyclic carbene (NHC) or mixed NHC/tertiary phosphine complexes [RhCl(cod)(sSIMes)], Na2[Rh(bmim)(cod)(mtppts)], and [Rh(bmim)(cod)(pta)]BF4 were synthetized and applied for the first time as catalysts in redox isomerization of allylic alcohols in aqueous media. [RhCl(cod)(sSIMes)] (with added sulfonated [...] Read more.
New water-soluble, N-heterocyclic carbene (NHC) or mixed NHC/tertiary phosphine complexes [RhCl(cod)(sSIMes)], Na2[Rh(bmim)(cod)(mtppts)], and [Rh(bmim)(cod)(pta)]BF4 were synthetized and applied for the first time as catalysts in redox isomerization of allylic alcohols in aqueous media. [RhCl(cod)(sSIMes)] (with added sulfonated triphenylphosphine) and [Rh(bmim)(cod)(pta)]BF4 catalyzed selectively the transformation of allylic alcohols to the corresponding ketones. The highest catalytic activity, TOF = 152 h−1 (TOF = (mol reacted substrate) × (mol catalyst × time)−1) was observed in redox isomerization of hept-1-en-3-ol ([S]/[cat] = 100). The catalysts were reused in the aqueous phase at least three times, with only modest loss of the catalytic activity and selectivity. Full article
(This article belongs to the Special Issue Catalysis in Heterocyclic and Organometallic Synthesis)
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Open AccessArticle
Synthesis and Investigation of Pinane-Based Chiral Tridentate Ligands in the Asymmetric Addition of Diethylzinc to Aldehydes
Catalysts 2020, 10(5), 474; https://doi.org/10.3390/catal10050474 - 26 Apr 2020
Abstract
A library of pinane-based chiral aminodiols, derived from natural (−)-β-pinene, were prepared and applied as chiral catalysts in the addition of diethylzinc to aldehydes. (−)-β-Pinene was reacted to provide 3-methylenenopinone, followed by a reduction of the carbonyl function to [...] Read more.
A library of pinane-based chiral aminodiols, derived from natural (−)-β-pinene, were prepared and applied as chiral catalysts in the addition of diethylzinc to aldehydes. (−)-β-Pinene was reacted to provide 3-methylenenopinone, followed by a reduction of the carbonyl function to give a key allylic alcohol intermediate. Stereoselective epoxidation of the latter and subsequent ring opening of the resulting oxirane with primary and secondary amines afforded aminodiols. The regioselectivity of the ring closure of the N-substituted secondary aminodiols with formaldehyde was examined and exclusive formation of oxazolidines was observed. Treatment of the allylic alcohol with benzyl bromide provided the corresponding O-benzyl derivative, which was transformed into O-benzyl aminodiols by aminolysis. Ring closure of the N-isopropyl aminodiol derivative with formaldehyde resulted in spirooxazolidine. The obtained potential catalysts were applied in the reaction of both aromatic and aliphatic aldehydes to diethylzinc providing moderate to good enantioselectivities (up to 87% ee). Through the use of molecular modeling at an ab initio level, this phenomenon was interpreted in terms of competing reaction pathways. Molecular modeling at the RHF/LANL2DZ level of theory was successfully applied for interpretation of the stereochemical outcome of the reactions leading to display excellent (R) enantioselectivity in the examined transformation. Full article
(This article belongs to the Special Issue Catalysis in Heterocyclic and Organometallic Synthesis)
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Open AccessArticle
Selective Hydration of Nitriles to Corresponding Amides in Air with Rh(I)-N-Heterocyclic Complex Catalysts
Catalysts 2020, 10(1), 125; https://doi.org/10.3390/catal10010125 - 16 Jan 2020
Abstract
A new synthetic method for obtaining [RhCl(cod)(NHC)] complexes (14) (cod = η4-1,5-cyclooctadiene, NHC = N-heterocyclic carbene: IMes, SIMes, IPr, and SIPr, respectively) is reported together with the catalytic properties of 14 in nitrile hydration. [...] Read more.
A new synthetic method for obtaining [RhCl(cod)(NHC)] complexes (14) (cod = η4-1,5-cyclooctadiene, NHC = N-heterocyclic carbene: IMes, SIMes, IPr, and SIPr, respectively) is reported together with the catalytic properties of 14 in nitrile hydration. In addition to the characterization of 14 in solution by 13C NMR spectroscopy, the structures of complexes 3, and 4 have been established also in the solid state with single-crystal X-ray diffraction analysis. The Rh(I)-NHC complexes displayed excellent catalytic activity in hydration of aromatic nitriles (up to TOF = 276 h−1) in water/2-propanol (1/1 v/v) mixtures in air. Full article
(This article belongs to the Special Issue Catalysis in Heterocyclic and Organometallic Synthesis)
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Open AccessArticle
Structural Properties and Catalytic Activity of Binary Poly (vinyl alcohol)/Al2O3 Nanocomposite Film for Synthesis of Thiazoles
Catalysts 2020, 10(1), 100; https://doi.org/10.3390/catal10010100 - 10 Jan 2020
Cited by 1
Abstract
A solution casting technique was applied to prepare a binary poly (vinyl alcohol)/Al2O3 nanocomposite. The structural properties of nanocomposite were investigated using Fourier-transform infrared spectra, field emission scanning electron microscope, energy dispersive X-ray analyses, and X-ray diffraction. The hybrid PVA/Al [...] Read more.
A solution casting technique was applied to prepare a binary poly (vinyl alcohol)/Al2O3 nanocomposite. The structural properties of nanocomposite were investigated using Fourier-transform infrared spectra, field emission scanning electron microscope, energy dispersive X-ray analyses, and X-ray diffraction. The hybrid PVA/Al2O3 film exhibited a conspicuous catalytic performance for synthesis of thiazole derivatives under mild reaction conditions. Moreover, the optimization of catalytic efficiency and reusability of this nanocomposite have been investigated. Full article
(This article belongs to the Special Issue Catalysis in Heterocyclic and Organometallic Synthesis)
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Review

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Open AccessReview
Recent Approaches to Chiral 1,4-Dihydropyridines and their Fused Analogues
Catalysts 2020, 10(9), 1019; https://doi.org/10.3390/catal10091019 - 04 Sep 2020
Abstract
The purpose of this review is to highlight recent developments in the synthesis of chiral 1,4-dihydropyridines and their fused analogues. 1,4-Dihydropyridines are among the most active calcium antagonists that are used for the treatment of hypertension. Enantiomers of unsymmetrical 1,4-dihydropyridines often show different [...] Read more.
The purpose of this review is to highlight recent developments in the synthesis of chiral 1,4-dihydropyridines and their fused analogues. 1,4-Dihydropyridines are among the most active calcium antagonists that are used for the treatment of hypertension. Enantiomers of unsymmetrical 1,4-dihydropyridines often show different biological activities and may have even an opposite action profile. Hantzsch synthesis usually produces racemic mixtures of unsymmetrical 1,4-dihydropyridines. Therefore, the development of stereoselective synthesis of 1,4-dihydropyridines is one of the priorities of medicinal chemistry. Over the years, numerous methodologies have been developed for the production of enantiopure 1,4-dihydropyridines, such as stereoselective synthesis using chiral auxiliaries and chiral cyclocondensation partners, chromatographical methods, resolution of diastereomeric 1,4-dihydropyridine salts, enzyme catalysed kinetic resolution, or asymmetrisation of ester groups of 1,4-dihydropyridines. These approaches have been studied in detail and are relatively well established. The catalytic asymmetric approach holds the greatest promise in delivering the most practical and widely applicable methods. Substantial progress has been made toward the development of enantioselective organocatalytic methods for the construction of the chiral dihydropyridines. However, most of them do not provide a convenient way to pharmacologically important 1,4-dihydropyridine-3,5-dicarboxylates. Organocatalytic enantioselective desymmetrisation of prochiral 1,4-dihydropyridine-3,5-dicarbaldehydes also has great promise in the synthesis of pharmacologically important 1,4-dihydropyridine-3,5-dicarboxylates. Full article
(This article belongs to the Special Issue Catalysis in Heterocyclic and Organometallic Synthesis)
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Planned Papers

The below list represents only planned manuscripts. Some of these manuscripts have not been received by the Editorial Office yet. Papers submitted to MDPI journals are subject to peer-review.

Title: Recent Advances in Oxidative Synthesis of Quinolines

Author: Liang-Hua Zou

Abstract: The research on the synthesis of quinolines has been extensively investigated during the past years due to their significant properties and applications in pharmaceuticals, useful ligands and materials. The traditional synthesis of quinolines, such as Friedländer quinoline synthesis and Combes quinoline synthesis, could date back to one century ago. So far, many methods have been developed to construction of structurally diverse and complex quinolines. Despite these advances, many of these procedures often suffered from strong acidic conditions, highly explosive, low yields, and expensive reagents. Therefore, the development of more efficient alternatives is still highly desirable.

Oxidative protocols have become an important means of synthesis of quinolines in the past years. Recently, significant advances in this field have witnessed a myriad of elegant reports on transition-metal catalyzed or transition-metal free reactions. These reactions indicate there are a great potential in exploiting the inherent reactivity of molecules through the combination use of an efficient catalyst, base, oxidant and solvent. This mini-review will focus on the synthesis of quinolines via oxidative annulation with or without the catalyst of transition-metals.

 

Title: Selective hydration of nitriles to amides in air with Rh(I)-N-heterocyclic catalysts

Authors: Csilla Enikő Czégéni, Sourav De, Antal Udvardy, Nóra Judit Derzsi, Gergely Papp,  Gábor Papp, and Ferenc Joó

Abstract: Although catalytic hydration of nitriles to amides is an often studied reaction, most of the catalysts are based on ruthenium, in contrast to rhodium complexes which are much less frequently applied as catalysts in this process. In this work we demonstrate that several easily available Rh(I)-NHC catalysts efficiently furnish the desired amides selectively, in air and under mild conditions.

Title: Non-K region disubstituted pyrenes (1,3-, 1,6- and 1,8-) by (hetero)aryl groups

Abstract: Disubstituted pyrenes at the non-K region by the same or different (hetero)aryl groups are in the increasing interest of scientists during the last decade due to their optical and photophysical properties. However, in that area, there is no systematization of the structures and synthesis methods and their limitations. Taking all into account I wrote the review article of the reported in the literature approaches to their synthesis starting from commercially available pyrene. Herein, the ways of obtaining of disubstituted intermediates based on bromination and acylation reaction were presented what is crucial in the determination of the possibility of further functionalization by using coupling, cycloaddition, condensation, etc. reactions. Moreover, the application of disubstituted pyrenes in the synthesis of 1,3,6,8-tetrasubstituted was also reviewed. The whole review demonstrates the direction in the chemistry of disubstituted pyrenes.

Author: Dawid Zych

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