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Special Issue "Palladium Catalysts"

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

Deadline for manuscript submissions: closed (15 May 2014)

Special Issue Editors

Guest Editor
Dr. Diego A. Alonso (Website)

Organic Chemistry Department and Institute for Organic Synthesis Alicante University, Apdo. 99, E-03080 Alicante, Spain
Phone: +34965903549
Interests: metal catalysis; asymmetric catalysis; organocatalysis; materials science; medicinal chemistry; carbocatalysis; green chemistry
Guest Editor
Dr. Isidro M. Pastor (Website)

Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, Alicante 03080, 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 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

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. Papers will be published continuously (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as 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 refereed through a peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed Open Access monthly 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 1800 CHF (Swiss Francs).

Keywords

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

Published Papers (7 papers)

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Research

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Open AccessArticle Palladium Catalyzed Heck Arylation of 2,3-Dihydrofuran—Effect of the Palladium Precursor
Molecules 2014, 19(6), 8402-8413; doi:10.3390/molecules19068402
Received: 26 May 2014 / Revised: 10 June 2014 / Accepted: 12 June 2014 / Published: 19 June 2014
Cited by 4 | PDF Full-text (502 KB) | HTML Full-text | XML Full-text
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) [...] 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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Open AccessArticle Palladium-Catalyzed Direct Addition of 2-Aminobenzonitriles to Sodium Arylsulfinates: Synthesis of o-Aminobenzophenones
Molecules 2014, 19(5), 6439-6449; doi:10.3390/molecules19056439
Received: 3 May 2014 / Revised: 15 May 2014 / Accepted: 19 May 2014 / Published: 20 May 2014
Cited by 4 | PDF Full-text (318 KB) | HTML Full-text | XML Full-text | Supplementary Files
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 [...] 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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Open AccessArticle Repetitive Two-Step Method for o,o,p- and o,p-Oligophenylene Synthesis through Pd-Catalyzed Cross-Coupling of Hydroxyterphenylboronic Acid
Molecules 2013, 18(12), 15207-15219; doi:10.3390/molecules181215207
Received: 16 October 2013 / Revised: 22 November 2013 / Accepted: 27 November 2013 / Published: 10 December 2013
Cited by 1 | PDF Full-text (447 KB) | HTML Full-text | XML Full-text | Supplementary Files
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 [...] 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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Open AccessArticle 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
Molecules 2013, 18(9), 10901-10911; doi:10.3390/molecules180910901
Received: 29 July 2013 / Revised: 21 August 2013 / Accepted: 2 September 2013 / Published: 4 September 2013
Cited by 3 | PDF Full-text (240 KB) | HTML Full-text | XML Full-text
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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Open AccessArticle Palladium-Catalyzed Synthesis of Natural and Unnatural 2-, 5-, and 7-Oxygenated Carbazole Alkaloids from N-Arylcyclohexane Enaminones
Molecules 2013, 18(9), 10334-10351; doi:10.3390/molecules180910334
Received: 5 July 2013 / Revised: 5 August 2013 / Accepted: 12 August 2013 / Published: 26 August 2013
Cited by 3 | PDF Full-text (330 KB) | HTML Full-text | XML Full-text
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 [...] 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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Open AccessArticle Enhanced Stability of CaO and/or La2O3 Promoted Pd/Al2O3 Egg-Shell Catalysts in Partial Oxidation of Methane to Syngas
Molecules 2013, 18(7), 8289-8297; doi:10.3390/molecules18078289
Received: 17 June 2013 / Revised: 5 July 2013 / Accepted: 9 July 2013 / Published: 15 July 2013
Cited by 2 | PDF Full-text (386 KB) | HTML Full-text | XML Full-text
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 [...] 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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Open AccessReview Palladium and Organocatalysis: An Excellent Recipe for Asymmetric Synthesis
Molecules 2013, 18(9), 10108-10121; doi:10.3390/molecules180910108
Received: 16 July 2013 / Revised: 9 August 2013 / Accepted: 15 August 2013 / Published: 22 August 2013
Cited by 7 | PDF Full-text (521 KB) | HTML Full-text | XML Full-text
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 [...] 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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