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Applications of Palladium-Catalyzed in Organic Chemistry
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Applications of Palladium-Catalyzed in Organic Chemistry

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

Deadline for manuscript submissions: closed (22 March 2022) | Viewed by 17777

Special Issue Editor

Prof. Dr. Lucia Veltri

E-Mail Website
Guest Editor
Department of Chemistry and Chemical Technologies, University of Calabria, Via Pietro Bucci 12/C, 87036 Arcavacata di Rende (CS), Italy
Interests: palladium-catalyzed reactions; homogeneous catalysis; carbonylation; heterocyclization; materials chemistry

Special Issue Information

Dear Colleagues,

Palladium is one of the most used elements in organic synthesis as it catalyzes a great variety of transformations. This ability is due to the stability of its oxidation states (0; +2) and the easy reversibility of transition from one state to another as well as its characteristic of interacting with different types of substrates and of tolerating many functional groups. In fact, palladium-based catalysts have been present in the literature since the second half of the 20th century and today involve every area of organic synthesis, from basic organic chemistry reactions such as hydrogenations, to advanced organic transformations such as pericyclic or carbonylation reactions. In general, Pd as a catalyst in organic chemistry is extensively used not only in C-C bond formation processes, but also in reactions involving the formation of new C-O or C-N or C-S bonds.

In recent decades, the possibility of forming new bonds easily and very often under mild conditions has directed scientific research towards the application of Pd-catalyzed reactions to the synthesis of compounds of industrial and pharmaceutical interest, with particular emphasis on the formation of new carbocyclic and heterocyclic compounds.

The aim of this Special Issue is therefore to report on recent advances in scientific research in the application of Pd-catalyzed reactions in organic synthesis. Both original research and reviews are welcome. Contributions concerning Pd-catalyzed reactions that lead to compounds with biological activity or with potential industrial applications will be particularly appreciated.

Prof. Dr. Lucia Veltri
Guest Editor

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Keywords

  • Palladium
  • cross-couplings
  • carbonylation reactions
  • cyclization reactions
  • homogeneous and heterogeneous catalysis

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Published Papers (5 papers)

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Research

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10 pages, 4150 KiB  
Article
Tandem Pd-Catalyzed Cyclization/Coupling of Non-Terminal Acetylenic Activated Methylenes with (Hetero)Aryl Bromides
by Aleksandra Błocka and Wojciech Chaładaj
Molecules 2022, 27(3), 630; https://doi.org/10.3390/molecules27030630 - 19 Jan 2022
Cited by 5 | Viewed by 2492
Abstract
We report a new method for a tandem Pd-catalyzed intramolecular addition of active methylene compounds to internal alkynes followed by coupling with aryl and heteroaryl bromides. Highly substituted vinylidenecyclopentanes were obtained with good yields, complete selectivity, and excellent functional group tolerance. A plausible [...] Read more.
We report a new method for a tandem Pd-catalyzed intramolecular addition of active methylene compounds to internal alkynes followed by coupling with aryl and heteroaryl bromides. Highly substituted vinylidenecyclopentanes were obtained with good yields, complete selectivity, and excellent functional group tolerance. A plausible mechanism, supported by DFT calculations, involves the oxidative addition of bromoarene to Pd(0), followed by cyclization and reductive elimination. The excellent regio- and stereoselectivity arises from the 5-exo-dig intramolecular addition of the enol form of the substrate to alkyne activated by the π-acidic Pd(II) center, postulated as the rate-determining step. Full article
(This article belongs to the Special Issue Applications of Palladium-Catalyzed in Organic Chemistry)
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13 pages, 15785 KiB  
Article
Non-C2-Symmetric Bis-Benzimidazolium Salt Applied in the Synthesis of Sterically Hindered Biaryls
by Yen-Hsin Chen, Shu-Jyun Huang, Tung-Yu Hsu, Pei-Yu Hung, Ting-Rong Wei, Dong-Sheng Lee and Ta-Jung Lu
Molecules 2021, 26(21), 6703; https://doi.org/10.3390/molecules26216703 - 5 Nov 2021
Cited by 3 | Viewed by 2336
Abstract
A novel non-C2-symmetric bis-benzimidazolium salt derived from (±)-valinol has been prepared by a simple and straightforward process in good yield. The structure of bis-benzimidazolium salt provided a bulky steric group on the ethylene bridge; which facilitates the catalytic efficacy [...] Read more.
A novel non-C2-symmetric bis-benzimidazolium salt derived from (±)-valinol has been prepared by a simple and straightforward process in good yield. The structure of bis-benzimidazolium salt provided a bulky steric group on the ethylene bridge; which facilitates the catalytic efficacy in the C(sp2)–C(sp2) formation. Its catalytic activity in Suzuki–Miyaura cross-coupling reaction of unactivated aryl chlorides has been found to have high efficacy in 1 mol% Pd loading. This protocol demonstrated the potential on the synthesis of sterically hindered biaryls. Full article
(This article belongs to the Special Issue Applications of Palladium-Catalyzed in Organic Chemistry)
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23 pages, 2279 KiB  
Article
Regioselective Mercury(I)/Palladium(II)-Catalyzed Single-Step Approach for the Synthesis of Imines and 2-Substituted Indoles
by Rsuini U. Gutiérrez, Mayra Hernández-Montes, Aarón Mendieta-Moctezuma, Francisco Delgado and Joaquín Tamariz
Molecules 2021, 26(13), 4092; https://doi.org/10.3390/molecules26134092 - 5 Jul 2021
Cited by 2 | Viewed by 3804
Abstract
An efficient synthesis of ketimines was achieved through a regioselective Hg(I)-catalyzed hydroamination of terminal acetylenes in the presence of anilines. The Pd(II)-catalyzed cyclization of these imines into the 2-substituted indoles was satisfactorily carried out by a C-H activation. In a single-step approach, a [...] Read more.
An efficient synthesis of ketimines was achieved through a regioselective Hg(I)-catalyzed hydroamination of terminal acetylenes in the presence of anilines. The Pd(II)-catalyzed cyclization of these imines into the 2-substituted indoles was satisfactorily carried out by a C-H activation. In a single-step approach, a variety of 2-substituted indoles were also generated via a Hg(I)/Pd(II)-catalyzed, one-pot, two-step process, starting from anilines and terminal acetylenes. The arylacetylenes proved to be more effective than the alkyl derivatives. Full article
(This article belongs to the Special Issue Applications of Palladium-Catalyzed in Organic Chemistry)
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Review

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57 pages, 31931 KiB  
Review
Palladium-Catalyzed Organic Reactions Involving Hypervalent Iodine Reagents
by Samata E. Shetgaonkar, Ritu Mamgain, Kotaro Kikushima, Toshifumi Dohi and Fateh V. Singh
Molecules 2022, 27(12), 3900; https://doi.org/10.3390/molecules27123900 - 17 Jun 2022
Cited by 19 | Viewed by 4273
Abstract
The chemistry of polyvalent iodine compounds has piqued the interest of researchers due to their role as important and flexible reagents in synthetic organic chemistry, resulting in a broad variety of useful organic molecules. These chemicals have potential uses in various functionalization procedures [...] Read more.
The chemistry of polyvalent iodine compounds has piqued the interest of researchers due to their role as important and flexible reagents in synthetic organic chemistry, resulting in a broad variety of useful organic molecules. These chemicals have potential uses in various functionalization procedures due to their non-toxic and environmentally friendly properties. As they are also strong electrophiles and potent oxidizing agents, the use of hypervalent iodine reagents in palladium-catalyzed transformations has received a lot of attention in recent years. Extensive research has been conducted on the subject of C—H bond functionalization by Pd catalysis with hypervalent iodine reagents as oxidants. Furthermore, the iodine(III) reagent is now often used as an arylating agent in Pd-catalyzed C—H arylation or Heck-type cross-coupling processes. In this article, the recent advances in palladium-catalyzed oxidative cross-coupling reactions employing hypervalent iodine reagents are reviewed in detail. Full article
(This article belongs to the Special Issue Applications of Palladium-Catalyzed in Organic Chemistry)
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23 pages, 14137 KiB  
Review
Advances in Palladium-Catalyzed Carboxylation Reactions
by Lucia Veltri, Roberta Amuso, Raffaella Mancuso and Bartolo Gabriele
Molecules 2022, 27(1), 262; https://doi.org/10.3390/molecules27010262 - 1 Jan 2022
Cited by 2 | Viewed by 3347
Abstract
In this short review, we highlight the advancements in the field of palladium-catalyzed carbon dioxide utilization for the synthesis of high value added organic molecules. The review is structured on the basis of the kind of substrate undergoing the Pd-catalyzed carboxylation process. Accordingly, [...] Read more.
In this short review, we highlight the advancements in the field of palladium-catalyzed carbon dioxide utilization for the synthesis of high value added organic molecules. The review is structured on the basis of the kind of substrate undergoing the Pd-catalyzed carboxylation process. Accordingly, after the introductory section, the main sections of the review will illustrate Pd-catalyzed carboxylation of olefinic substrates, acetylenic substrates, and other substrates (aryl halides and triflates). Full article
(This article belongs to the Special Issue Applications of Palladium-Catalyzed in Organic Chemistry)
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