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Molbank
Special Issues
Metal-Catalyzed Synthesis
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Metal-Catalyzed Synthesis

A special issue of Molbank (ISSN 1422-8599). This special issue belongs to the section "Organic Synthesis".

Deadline for manuscript submissions: closed (31 October 2021) | Viewed by 18366

Special Issue Editor

Prof. Dr. Bartolo Gabriele

E-Mail Website
Guest Editor
Laboratory of Industrial and Synthetic Organic Chemistry (LISOC), Department of Chemistry and Chemical Technologies, University of Calabria, Via Pietro Bucci, 12/C, 87036 Arcavacata di Rende, Italy
Interests: new syntheses of high value added molecules through catalytic assembly of simple units; innovative syntheses of heterocyclic molecules of pharmaceutical; agrochemical; applicative interest; carbonylation chemistry; use of non-conventional solvents in organic synthesis; synthesis and semi-synthesis of bioactive compounds of pharmaceutical or agrochemical interest; synthesis of new materials for advanced applications; extraction; characterization; evaluation of the biological activity of bioactive principles from natural matrices
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

This Special Issue is devoted to metal-catalyzed synthesis, which is of one of the most important tools in modern synthetic organic chemistry. In fact, under the catalytic action of a metal center, stabilized by suitable ligands, different small molecules can be sequentially activated to afford complex, high-value added compounds in one synthetic step. Although enormous progress has been made in this field during the last few decades, this kind of chemistry is still very attractive and important, and will continue to attract the interest of chemists, both in academia and industry around the world.

Prof. Dr. Bartolo Gabriele
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. Molbank is an international peer-reviewed open access quarterly 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 500 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

  • catalysis
  • heterogeneous catalysis
  • homogeneous catalysis
  • metal-catalyzed reactions
  • organic synthesis promoted by metal catalysts

Published Papers (7 papers)

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Research

3 pages, 532 KiB  
Short Note
N,N-Bis(4′-(hexyloxy)-[1,1′-biphenyl]-4-yl)thiophen-2-amine
by Timofey N. Chmovzh and Oleg A. Rakitin
Molbank 2021, 2021(4), M1290; https://doi.org/10.3390/M1290 - 21 Oct 2021
Viewed by 2025
Abstract
N,N-Diarylthiophen-2-amine units are of great interest for the synthesis of optoelectronic devices. In this communication, N,N-bis (4′-(hexyloxy)-[1,1′-biphenyl]-4-yl)thiophen-2-amine was obtained by means of a Buchwald–Hartwig cross-coupling reaction of bis(4′-(hexyloxy)-[1,1′-biphenyl]-4-yl)amine and 2-bromothiophene in the presence of tris(dibenzylideneacetone)dipalladium(0), tri-tert [...] Read more.
N,N-Diarylthiophen-2-amine units are of great interest for the synthesis of optoelectronic devices. In this communication, N,N-bis (4′-(hexyloxy)-[1,1′-biphenyl]-4-yl)thiophen-2-amine was obtained by means of a Buchwald–Hartwig cross-coupling reaction of bis(4′-(hexyloxy)-[1,1′-biphenyl]-4-yl)amine and 2-bromothiophene in the presence of tris(dibenzylideneacetone)dipalladium(0), tri-tert-butyl phosphine and sodium tert-butanolate. The structure of newly synthesized compounds was established by means of elemental analysis, high-resolution mass spectrometry, 1H, 13C NMR, IR and UV spectroscopy and mass-spectrometry. Full article
(This article belongs to the Special Issue Metal-Catalyzed Synthesis)
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Graphical abstract

12 pages, 3788 KiB  
Short Note
Naphthalen-2-yl 1-(benzamido(diethoxyphosphoryl)methyl)-1H-1,2,3-triazole-4-carboxylate
by Serigne Abdou Khadir Fall, Sara Hajib, Oumaima Karai, Salaheddine Boukhssas, Younas Aouine, Mohamed Akhazzane, Brahim Labriti, Hassane Faraj and Anouar Alami
Molbank 2021, 2021(4), M1285; https://doi.org/10.3390/M1285 - 04 Oct 2021
Cited by 1 | Viewed by 2334
Abstract
We have previously published new biheterocyclic phospohonic α-amino esters of the 1,2,3-triazole-benzimidazole and 1,2,3-triazole-carbazole type. The aim of the present paper was to describe a new phosponic aminoester bearing a triazole ring substituted in position 5 by an ester group. Thus, according to [...] Read more.
We have previously published new biheterocyclic phospohonic α-amino esters of the 1,2,3-triazole-benzimidazole and 1,2,3-triazole-carbazole type. The aim of the present paper was to describe a new phosponic aminoester bearing a triazole ring substituted in position 5 by an ester group. Thus, according to the same catalytic process used previously, the compound naphthalen-2-yl 1-(benzamido(diethoxyphosphoryl)methyl)-1H-1,2,3-triazole-4-carboxylate was synthesized with an excellent yield and high regioselectivity via the copper (I)-catalyzed alkyne–azide cycloaddition reaction (CuAAC), using diethyl (α-azido(benzamido)methyl)phosphonate (1) as a dipole and 2- naphthyl propiolate as a dipolarophile (2). The structure of the new compound was fully characterized by 1D (31P, 1H-, 13C-) and 2D (1H-1H and 1H-, 13C-) NMR spectroscopy, IR, and HRMS. Full article
(This article belongs to the Special Issue Metal-Catalyzed Synthesis)
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Figure 1

4 pages, 347 KiB  
Short Note
tert-Butyl Bis(4′-(Hexyloxy)-[1,1′-biphenyl]-4-yl)carbamate
by Timofey N. Chmovzh and Oleg A. Rakitin
Molbank 2021, 2021(3), M1247; https://doi.org/10.3390/M1247 - 05 Jul 2021
Cited by 1 | Viewed by 1840
Abstract
New donor building blocks, i.e., triarylamino derivatives, are of great interest for the production of organic photovoltaic materials. In this communication, bis(4′-(hexyloxy)-[1,1′-biphenyl]-4-yl)amine was synthesized in a two-step process via hydrolysis of its tert-butyl carbamate derivative. tert-Butyl bis(4′-(hexyloxy)-[1,1′-biphenyl]-4-yl)carbamate was obtained by Suzuki [...] Read more.
New donor building blocks, i.e., triarylamino derivatives, are of great interest for the production of organic photovoltaic materials. In this communication, bis(4′-(hexyloxy)-[1,1′-biphenyl]-4-yl)amine was synthesized in a two-step process via hydrolysis of its tert-butyl carbamate derivative. tert-Butyl bis(4′-(hexyloxy)-[1,1′-biphenyl]-4-yl)carbamate was obtained by Suzuki cross-coupling reaction of tert-butyl bis(4-bromophenyl)carbamate and (4-(hexyloxy)phenyl)boronic acid in the presence of tetrakis(triphenylphosphine)palladium(0). The structure of newly synthesized compounds was established by means of elemental analysis, high resolution mass-spectrometry, 1H, 13C-NMR, IR and UV spectroscopy and mass-spectrometry. Full article
(This article belongs to the Special Issue Metal-Catalyzed Synthesis)
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Scheme 1

4 pages, 415 KiB  
Short Note
2′-Chloro-4-(1-methyl-1H-imidazol-2-yl)-2,4′-bipyridine
by Dhafer Saber Zinad, Dunya L. AL-Duhaidahaw and Ahmed Al-Amiery
Molbank 2019, 2019(1), M1040; https://doi.org/10.3390/M1040 - 22 Dec 2018
Cited by 2 | Viewed by 1925
Abstract
The compound 2′-chloro-4-(1-methyl-1H-imidazol-2-yl)-2,4′-bipyridine was obtained with a good yield by the reaction of 2-chloro-4-(1-methyl-1H-imidazol-2-yl)pyridine with (2-chloropyridin-4-yl)boronic acid and structurally characterized by nuclear magnetic resonance (1H-NMR and 13C-NMR), thin-layer chromatography–mass spectrometry (TLC–MS), HPLC, gas chromatography–mass spectrometry (GC–MS), [...] Read more.
The compound 2′-chloro-4-(1-methyl-1H-imidazol-2-yl)-2,4′-bipyridine was obtained with a good yield by the reaction of 2-chloro-4-(1-methyl-1H-imidazol-2-yl)pyridine with (2-chloropyridin-4-yl)boronic acid and structurally characterized by nuclear magnetic resonance (1H-NMR and 13C-NMR), thin-layer chromatography–mass spectrometry (TLC–MS), HPLC, gas chromatography–mass spectrometry (GC–MS), and elemental analysis. The functionalization of the pyridine was achieved by the palladium-catalyzed Suzuki–Miyaura carbon–carbon cross-coupling reaction that afforded the target compound. Full article
(This article belongs to the Special Issue Metal-Catalyzed Synthesis)
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Scheme 1

5 pages, 378 KiB  
Short Note
5-Chloro-8-{[1-(2-chlorobenzyl)-1H-1,2,3-triazol-4-yl]methoxy}quinoline
by Luz Karime Luna Parada and Vladimir V. Kouznetsov
Molbank 2019, 2019(1), M1038; https://doi.org/10.3390/M1038 - 20 Dec 2018
Cited by 4 | Viewed by 2757
Abstract
The title quinoline derivative, 5-chloro-8-{[1-(2-chlorobenzyl)-1H-1,2,3-triazol-4-yl]methoxy}quinoline, was synthesized in a common three-step procedure from 5-chloro-8-hydroxyquinoline using O-propargylation reaction/copper-catalyzed 1,3-dipolar cycloaddition sequence. The structure of the compound was fully characterized by FT-IR, 1H- and 13C-NMR, GC-MS, and elemental analysis. Its [...] Read more.
The title quinoline derivative, 5-chloro-8-{[1-(2-chlorobenzyl)-1H-1,2,3-triazol-4-yl]methoxy}quinoline, was synthesized in a common three-step procedure from 5-chloro-8-hydroxyquinoline using O-propargylation reaction/copper-catalyzed 1,3-dipolar cycloaddition sequence. The structure of the compound was fully characterized by FT-IR, 1H- and 13C-NMR, GC-MS, and elemental analysis. Its physicochemical parameters (Lipinski’s descriptors) were also calculated using the Molinspiration Cheminformatics software. The hybrid obtained could be an interesting model for antifungal bio-essays or a suitable precursor in the synthesis of more complex triazolyl-quinoline hybrids, potential pharmacological agents. Full article
(This article belongs to the Special Issue Metal-Catalyzed Synthesis)
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Graphical abstract

4 pages, 491 KiB  
Short Note
(S)-4-Isopropyl-5,5-diphenyloxazolidin-2-one
by Raffaella Mancuso, Rossana Miliè, Ida Ziccarelli, Mariangela Novello, Nicola Della Ca’ and Bartolo Gabriele
Molbank 2018, 2018(3), M1017; https://doi.org/10.3390/M1017 - 31 Aug 2018
Cited by 1 | Viewed by 2554
Abstract
(S)-4-Isopropyl-5,5-diphenyloxazolidin-2-one has been synthesized for the first time by the enantiospecific oxidative carbonylation of commercially available (S)-2-amino-3-methyl-1,1-diphenylbutan-1-ol. The cyclocarbonylation reaction was carried out at 100 °C in 1,2-dimethoxyethane (DME) as the solvent for 15 h, under 20 atm of [...] Read more.
(S)-4-Isopropyl-5,5-diphenyloxazolidin-2-one has been synthesized for the first time by the enantiospecific oxidative carbonylation of commercially available (S)-2-amino-3-methyl-1,1-diphenylbutan-1-ol. The cyclocarbonylation reaction was carried out at 100 °C in 1,2-dimethoxyethane (DME) as the solvent for 15 h, under 20 atm of a 4:1 mixture of CO–air and in the presence of the catalytic system PdI2/KI (substrate:KI:PdI2 molar ratio = 100:10:1), to give the oxazolidinone derivative in 81% isolated yield. Full article
(This article belongs to the Special Issue Metal-Catalyzed Synthesis)
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Graphical abstract

9 pages, 1858 KiB  
Communication
Gold-Catalyzed Synthesis of 2-Sulfenylspiroindolenines via Spirocyclizations
by Valentin Magné, Pascal Retailleau, Angela Marinetti, Arnaud Voituriez and Xavier Guinchard
Molbank 2018, 2018(1), M985; https://doi.org/10.3390/M985 - 23 Feb 2018
Cited by 8 | Viewed by 3386
Abstract
2-Phenylsulfenyl-N-propargyl tryptamines have been prepared by electrophilic sulfuration of the corresponding tryptamines. These compounds undergo gold-catalyzed spirocyclizations to the corresponding 2-phenylthiospiroindolenines in good yields. The compounds were analyzed by NMR experiments, infrared, mass spectra and X-ray diffraction. This method provides a [...] Read more.
2-Phenylsulfenyl-N-propargyl tryptamines have been prepared by electrophilic sulfuration of the corresponding tryptamines. These compounds undergo gold-catalyzed spirocyclizations to the corresponding 2-phenylthiospiroindolenines in good yields. The compounds were analyzed by NMR experiments, infrared, mass spectra and X-ray diffraction. This method provides a new efficient entry to the synthesis of 2-sulfenyl spiroindolic compounds. Full article
(This article belongs to the Special Issue Metal-Catalyzed Synthesis)
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