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Palladium Catalysts
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Palladium Catalysts

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

Deadline for manuscript submissions: closed (15 May 2014) | Viewed by 49955

Special Issue Editors

Dr. Diego A. Alonso

E-Mail Website
Guest Editor
Department of Organic Chemistry and Institute of Organic Synthesis (ISO), University of Alicante, P.O. Box 99, 03080 Alicante, Spain
Interests: metal catalysis; asymmetric catalysis; organocatalysis; materials science; medicinal chemistry; carbocatalysis; green chemistry
Special Issues, Collections and Topics in MDPI journals
Dr. Isidro M. Pastor

E-Mail Website
Guest Editor
Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain
Interests: application of organometallic compounds in organic synthesis; synthesis of heterocyclic derivatives and their application as ligands in homogeneous and heterogeneous (MOFs) catalysts
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Palladium-catalyzed reactions are of vital importance in organic synthesis. Palladium catalysts have played a fundamental role in the development of a wide variety of transformations due to its versatility and high functional group tolerance. Indeed, palladium-catalyzed reactions are nowadays routinely employed as powerful synthetic tools both in academia and industry. Particularly interesting have resulted the advances in new catalyst development which has enable to perform difficult transformations with unactivated substrates using low catalyst loadings under mild and green reaction conditions.

This special issue will mainly focus on the latest advances and novel trends in the field of palladium catalysts ranging from the basic research and characterization studies to the development of highly active catalysts and their application in different redox processes, cross-coupling as well as C-H activation reactions.

Dr. Diego A. Alonso
Dr. Isidro M. Pastor
Guest Editors

Submission

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Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 1800 CHF (Swiss francs).

Keywords

  • palladium
  • cross-coupling
  • organic chemistry
  • green chemistry
  • heterogeneous chemistry
  • C-H activation
  • water
  • redox processes

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Published Papers (7 papers)

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Research

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502 KiB  
Article
Palladium Catalyzed Heck Arylation of 2,3-Dihydrofuran—Effect of the Palladium Precursor
by Adam Morel, Anna M. Trzeciak and Juliusz Pernak
Molecules 2014, 19(6), 8402-8413; https://doi.org/10.3390/molecules19068402 - 19 Jun 2014
Cited by 11 | Viewed by 7127
Abstract
Heck arylation of 2,3-dihydrofuran with iodobenzene was carried out in systems consisting of different palladium precursors (Pd2(dba)3, Pd(acac)2, PdCl2(cod), [PdCl(allyl)]2, PdCl2(PhCN)2, PdCl2(PPh3)2) and [...] Read more.
Heck arylation of 2,3-dihydrofuran with iodobenzene was carried out in systems consisting of different palladium precursors (Pd2(dba)3, Pd(acac)2, PdCl2(cod), [PdCl(allyl)]2, PdCl2(PhCN)2, PdCl2(PPh3)2) and ionic liquids (CILs) with L-prolinate or L-lactate anions. All the tested CILs caused remarkable increases of the conversion values and in all of the reactions 2-phenyl-2,3-dihydrofuran (3) was obtained as the main product with a yield of up to 59.2%. The highest conversions of iodobenzene were achieved for the [PdCl(allyl)]2 precursor. Formation of Pd(0) nanoparticles, representing the resting state of the catalyst, was evidenced by TEM. Full article
(This article belongs to the Special Issue Palladium Catalysts)
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318 KiB  
Article
Palladium-Catalyzed Direct Addition of 2-Aminobenzonitriles to Sodium Arylsulfinates: Synthesis of o-Aminobenzophenones
by Jiuxi Chen, Jianjun Li and Weike Su
Molecules 2014, 19(5), 6439-6449; https://doi.org/10.3390/molecules19056439 - 20 May 2014
Cited by 16 | Viewed by 7632
Abstract
The first example of the palladium-catalyzed synthesis of o-aminobenzophenones in moderate to excellent yields via a direct addition of sodium arylsulfinates to unprotected 2-aminobenzonitriles was reported. A plausible mechanism for the formation of o-aminobenzophenones involving desulfination and addition reactions was proposed. [...] Read more.
The first example of the palladium-catalyzed synthesis of o-aminobenzophenones in moderate to excellent yields via a direct addition of sodium arylsulfinates to unprotected 2-aminobenzonitriles was reported. A plausible mechanism for the formation of o-aminobenzophenones involving desulfination and addition reactions was proposed. The utility of this transformation was demonstrated by its compatibility with a wide range of functional groups. Thus, the method represents a convenient and practical strategy for synthesis of o-aminobenzophenones. Full article
(This article belongs to the Special Issue Palladium Catalysts)
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447 KiB  
Article
Repetitive Two-Step Method for o,o,p- and o,p-Oligophenylene Synthesis through Pd-Catalyzed Cross-Coupling of Hydroxyterphenylboronic Acid
by Miyuki Yamaguchi, Takeshi Kimura, Naomi Shinohara and Kei Manabe
Molecules 2013, 18(12), 15207-15219; https://doi.org/10.3390/molecules181215207 - 10 Dec 2013
Cited by 5 | Viewed by 5726
Abstract
A repetitive two-step method involving the Pd-catalyzed Suzuki-Miyaura coupling of hydroxyterphenylboronic acid and the subsequent nonaflation of the hydroxy group has been developed for the synthesis of oligophenylenes. This method readily afforded o,o,p- and o,p-oligophenylenes [...] Read more.
A repetitive two-step method involving the Pd-catalyzed Suzuki-Miyaura coupling of hydroxyterphenylboronic acid and the subsequent nonaflation of the hydroxy group has been developed for the synthesis of oligophenylenes. This method readily afforded o,o,p- and o,p-oligophenylenes with defined chain lengths. X-ray crystallography was employed to obtain the structure of the o,p-oligophenylene 9-mer. Full article
(This article belongs to the Special Issue Palladium Catalysts)
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240 KiB  
Article
A Recyclable Palladium-Catalyzed Synthesis of 2-Methylene-2,3-Dihydrobenzofuran-3-ols by Cycloisomerization of 2-(1-Hydroxyprop-2-ynyl)phenols in Ionic Liquids
by Raffaella Mancuso and Bartolo Gabriele
Molecules 2013, 18(9), 10901-10911; https://doi.org/10.3390/molecules180910901 - 4 Sep 2013
Cited by 10 | Viewed by 5483
Abstract
A recyclable palladium-catalyzed synthesis of 2-methylene-2,3-dihydrobenzofuran-3-ols 2 by heterocyclization of 2-(1-hydroxyprop-2-ynyl)phenols 1 in an ionic liquid medium (BmimBF4) is presented. The process takes place under relatively mild conditions (100 °C, 5 h) in the presence of catalytic amounts (2 mol %) [...] Read more.
A recyclable palladium-catalyzed synthesis of 2-methylene-2,3-dihydrobenzofuran-3-ols 2 by heterocyclization of 2-(1-hydroxyprop-2-ynyl)phenols 1 in an ionic liquid medium (BmimBF4) is presented. The process takes place under relatively mild conditions (100 °C, 5 h) in the presence of catalytic amounts (2 mol %) of PdI2 in conjunction with KI (5 equiv with respect to PdI2) and an organic base, such as morpholine (1 equiv with respect to 1), to give 2 in high yields (70%–86%). The PdI2-KI catalytic system could be recycled up to six times without appreciable loss of activity. Moreover, products 2 could be easily converted in a one-pot fashion into 2-hydroxymethylbenzofurans 3 (52%–71%, based on 1) and 2-methoxymethylbenzofurans 4 (52%–80%, based on 1) by acid-catalyzed allylic isomerization or allylic nucleophilic substitution. Full article
(This article belongs to the Special Issue Palladium Catalysts)
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330 KiB  
Article
Palladium-Catalyzed Synthesis of Natural and Unnatural 2-, 5-, and 7-Oxygenated Carbazole Alkaloids from N-Arylcyclohexane Enaminones
by Rafael Bautista, Pablo A. Montoya, Araceli Rebollar, Eleuterio Burgueño and Joaquín Tamariz
Molecules 2013, 18(9), 10334-10351; https://doi.org/10.3390/molecules180910334 - 26 Aug 2013
Cited by 27 | Viewed by 8945
Abstract
A palladium-catalyzed synthesis of the carbazole framework is described, including the preparation of 2-, 5-, and 7-oxygenated natural and unnatural carbazole alkaloids. A series of N-arylcyclohexane enaminones, generated by condensation of cyclohexane-1,3-dione with diverse anilines, were aromatized by a Pd(0)-catalyzed thermal treatment [...] Read more.
A palladium-catalyzed synthesis of the carbazole framework is described, including the preparation of 2-, 5-, and 7-oxygenated natural and unnatural carbazole alkaloids. A series of N-arylcyclohexane enaminones, generated by condensation of cyclohexane-1,3-dione with diverse anilines, were aromatized by a Pd(0)-catalyzed thermal treatment to afford the corresponding diarylamines. The latter were submitted to a Pd(II)-catalyzed cyclization and methylation processes to provide the desired carbazoles, including clausine V. Following an inverse strategy, a new and short total synthesis of glycoborine is also reported. Full article
(This article belongs to the Special Issue Palladium Catalysts)
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386 KiB  
Article
Enhanced Stability of CaO and/or La2O3 Promoted Pd/Al2O3 Egg-Shell Catalysts in Partial Oxidation of Methane to Syngas
by Jinlong Wang, Hongbo Yu, Zhen Ma and Shenghu Zhou
Molecules 2013, 18(7), 8289-8297; https://doi.org/10.3390/molecules18078289 - 15 Jul 2013
Cited by 9 | Viewed by 6357
Abstract
An egg-shell Pd/Al2O3 catalyst showed higher activity than a regular Pd/Al2O3 catalyst in the partial oxidation of methane to syngas, but a common problem of this reaction is the catalyst deactivation on stream. We attempted to modify [...] Read more.
An egg-shell Pd/Al2O3 catalyst showed higher activity than a regular Pd/Al2O3 catalyst in the partial oxidation of methane to syngas, but a common problem of this reaction is the catalyst deactivation on stream. We attempted to modify the egg-shell catalyst via impregnation with some metal oxide additives. Although the addition of MgO did not show any beneficial effect, the addition of CaO and/or La2O3 significantly improved the stability due to the suppression of carbon deposition and phase transformation of the Al2O3 support. The catalysts were characterized by X-ray diffraction (XRD), N2 adsorption-desorption, and thermogravimetric analysis (TGA). Full article
(This article belongs to the Special Issue Palladium Catalysts)
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Review

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521 KiB  
Review
Palladium and Organocatalysis: An Excellent Recipe for Asymmetric Synthesis
by M. Ángeles Fernández-Ibañez, Beatriz Maciá, Diego A. Alonso and Isidro M. Pastor
Molecules 2013, 18(9), 10108-10121; https://doi.org/10.3390/molecules180910108 - 22 Aug 2013
Cited by 22 | Viewed by 7787
Abstract
The dual activation of simple substrates by the combination of organocatalysis and palladium catalysis has been successfully applied in a variety of different asymmetric transformations. Thus, the asymmetric a-allylation of carbonyl compounds, a-fluorination of acyl derivatives, decarboxylative protonation of β-dicarbonyl compounds, cyclization reactions [...] Read more.
The dual activation of simple substrates by the combination of organocatalysis and palladium catalysis has been successfully applied in a variety of different asymmetric transformations. Thus, the asymmetric a-allylation of carbonyl compounds, a-fluorination of acyl derivatives, decarboxylative protonation of β-dicarbonyl compounds, cyclization reactions of alkynyl carbonyl compounds and β-functionalization of aldehydes have been efficiently achieved employing this double-catalytic methodology. Full article
(This article belongs to the Special Issue Palladium Catalysts)
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