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Catalysts
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Palladium Catalysts for Cross-Coupling Reaction
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Palladium Catalysts for Cross-Coupling Reaction

A special issue of Catalysts (ISSN 2073-4344). This special issue belongs to the section "Catalytic Materials".

Deadline for manuscript submissions: closed (15 June 2014) | Viewed by 62051

Special Issue Editor

Prof. Dr. Kei Manabe

E-Mail Website
Guest Editor
School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan
Interests: cross coupling; palladium catalyst; homogeneous/heterogeneous catalyst; selective reaction; allylic substitution; carbonylation; C-H activation; reaction mechanism; organometallic chemistry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Palladium is definitely one of the most important transition metals in organic synthesis. The significance of palladium catalysts is evident by the fact that the Nobel Prize in Chemistry 2010 was awarded to Richard F. Heck, Ei-ichi Negishi, and Akira Suzuki “for palladium-catalyzed cross couplings in organic synthesis”. Though the cross coupling chemistry emerged during the 1970s, this research field is still evolving and considerable attention is being given to investigate new catalytic reactions such as stereo- and site-selective cross coupling, reactions with less reactive leaving groups, and cross coupling at C-H positions. This special issue will cover significant development in the exciting field of palladium-catalyzed cross coupling.

Prof. Dr. Kei Manabe
Guest Editor

Manuscript Submission Information

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Keywords

  • cross coupling
  • palladium catalyst
  • homogeneous/heterogeneous catalyst
  • selective reaction
  • allylic substitution
  • carbonylation
  • C-H activation
  • reaction mechanism
  • organometallic chemistry

Published Papers (7 papers)

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Editorial

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216 KiB  
Editorial
Palladium Catalysts for Cross-Coupling Reaction
by Kei Manabe
Catalysts 2015, 5(1), 38-39; https://doi.org/10.3390/catal5010038 - 22 Jan 2015
Cited by 9 | Viewed by 5115
Abstract
Palladium-catalyzed cross-coupling reactions constitute one of the most important and useful transformations in transition metal-catalyzed reactions [1–3]. Although this research field emerged in the 1970s, it is still attracting considerable attention in synthetic and organometallic chemistry. New catalysts and catalytic systems are being [...] Read more.
Palladium-catalyzed cross-coupling reactions constitute one of the most important and useful transformations in transition metal-catalyzed reactions [1–3]. Although this research field emerged in the 1970s, it is still attracting considerable attention in synthetic and organometallic chemistry. New catalysts and catalytic systems are being developed to further expand the utility of the reactions. This Special Issue on “Palladium Catalysts for Cross-Coupling Reaction” covers the diverse aspects of the ever-evolving field of palladium catalysts in cross coupling chemistry.[...] Full article
(This article belongs to the Special Issue Palladium Catalysts for Cross-Coupling Reaction)

Research

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99 KiB  
Article
Palladium on Carbon-Catalyzed Suzuki-Miyaura Coupling Reaction Using an Efficient and Continuous Flow System
by Tomohiro Hattori, Aya Tsubone, Yoshinari Sawama, Yasunari Monguchi and Hironao Sajiki
Catalysts 2015, 5(1), 18-25; https://doi.org/10.3390/catal5010018 - 12 Jan 2015
Cited by 39 | Viewed by 10810
Abstract
The continuous flow Suzuki-Miyaura reaction between various haloarenes and arylboronic acids was successfully achieved within only ca. 20 s during the single-pass through a cartridge filled with palladium on carbon (Pd/C). No palladium leaching was observed in the collected reaction solution by atomic [...] Read more.
The continuous flow Suzuki-Miyaura reaction between various haloarenes and arylboronic acids was successfully achieved within only ca. 20 s during the single-pass through a cartridge filled with palladium on carbon (Pd/C). No palladium leaching was observed in the collected reaction solution by atomic absorption spectrometry (detection limit: 1 ppm). Full article
(This article belongs to the Special Issue Palladium Catalysts for Cross-Coupling Reaction)
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259 KiB  
Article
Palladium-Catalyzed Polyfluorophenylation of Porphyrins with Bis(polyfluorophenyl)zinc Reagents
by Noriaki Sugita, Satoshi Hayashi, Sawa Ishii and Toshikatsu Takanami
Catalysts 2013, 3(4), 839-852; https://doi.org/10.3390/catal3040839 - 22 Oct 2013
Cited by 11 | Viewed by 6153
Abstract
A facile and efficient method for the synthesis of pentafluorophenyl- and related polyfluorophenyl-substituted porphyrins has been achieved via palladium-catalyzed cross-coupling reactions of brominated porphyrins with bis(polyfluorophenyl)zinc reagents. The reaction is applicable to a variety of free-base bromoporphyrins, their metal complexes, and a number [...] Read more.
A facile and efficient method for the synthesis of pentafluorophenyl- and related polyfluorophenyl-substituted porphyrins has been achieved via palladium-catalyzed cross-coupling reactions of brominated porphyrins with bis(polyfluorophenyl)zinc reagents. The reaction is applicable to a variety of free-base bromoporphyrins, their metal complexes, and a number of bis(polyfluorophenyl)zinc reagents. Full article
(This article belongs to the Special Issue Palladium Catalysts for Cross-Coupling Reaction)
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408 KiB  
Article
Mechanistic Studies for Synthesis of Bis(indolyl)methanes: Pd-Catalyzed C–H Activation of Indole–Carboxylic Acids with Benzyl Alcohols in Water
by Hidemasa Hikawa, Hideharu Suzuki, Yuusaku Yokoyama and Isao Azumaya
Catalysts 2013, 3(2), 486-500; https://doi.org/10.3390/catal3020486 - 16 May 2013
Cited by 33 | Viewed by 9390
Abstract
A method for synthesis without protecting groups of bis(indolyl)methanes by the (η3-benzyl)palladium system generated from a palladium catalyst and benzyl alcohol in water is developed. This domino protocol involves C3–H bond activation/benzylation of indole–carboxylic acids and benzylic C–H functionalization. Mechanistic studies [...] Read more.
A method for synthesis without protecting groups of bis(indolyl)methanes by the (η3-benzyl)palladium system generated from a palladium catalyst and benzyl alcohol in water is developed. This domino protocol involves C3–H bond activation/benzylation of indole–carboxylic acids and benzylic C–H functionalization. Mechanistic studies indicate that the (η3-benzyl)palladium(II) complex, which is formed via oxidative addition of benzyl alcohol 2 to a Pd(0) species, activates the C–H bond at the C3-position of indole 1. Notably, water plays an important role in our catalytic system for sp3 C–O bond activation and stabilization of OH− by hydration for the smooth generation of the activated Pd(II) cation species, as well as for nucleophilic attack of indoles to hydrated benzyl alcohols. Full article
(This article belongs to the Special Issue Palladium Catalysts for Cross-Coupling Reaction)
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Review

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2029 KiB  
Review
Palladium-Catalyzed Cross-Coupling Reactions of Perfluoro Organic Compounds
by Masato Ohashi and Sensuke Ogoshi
Catalysts 2014, 4(3), 321-345; https://doi.org/10.3390/catal4030321 - 10 Sep 2014
Cited by 16 | Viewed by 9439
Abstract
In this review, we summarize our recent development of palladium(0)-catalyzed cross-coupling reactions of perfluoro organic compounds with organometallic reagents. The oxidative addition of a C–F bond of tetrafluoroethylene (TFE) to palladium(0) was promoted by the addition of lithium iodide, affording a trifluorovinyl palladium(II) [...] Read more.
In this review, we summarize our recent development of palladium(0)-catalyzed cross-coupling reactions of perfluoro organic compounds with organometallic reagents. The oxidative addition of a C–F bond of tetrafluoroethylene (TFE) to palladium(0) was promoted by the addition of lithium iodide, affording a trifluorovinyl palladium(II) iodide. Based on this finding, the first palladium-catalyzed cross-coupling reaction of TFE with diarylzinc was developed in the presence of lithium iodide, affording α,β,β-trifluorostyrene derivatives in excellent yield. This coupling reaction was expanded to the novel Pd(0)/PR3-catalyzed cross-coupling reaction of TFE with arylboronates. In this reaction, the trifluorovinyl palladium(II) fluoride was a key reaction intermediate that required neither an extraneous base to enhance the reactivity of organoboronates nor a Lewis acid additive to promote the oxidative addition of a C–F bond. In addition, our strategy utilizing the synergetic effect of Pd(0) and lithium iodide could be applied to the C–F bond cleavage of unreactive hexafluorobenzene (C6F6), leading to the first Pd(0)-catalyzed cross-coupling reaction of C6F6 with diarylzinc compounds. Full article
(This article belongs to the Special Issue Palladium Catalysts for Cross-Coupling Reaction)
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500 KiB  
Review
Catalyst-Controlled Site-Selectivity Switching in Pd-Catalyzed Cross-Coupling of Dihaloarenes
by Kei Manabe and Miyuki Yamaguchi
Catalysts 2014, 4(3), 307-320; https://doi.org/10.3390/catal4030307 - 20 Aug 2014
Cited by 25 | Viewed by 9031
Abstract
Pd-catalyzed, site-selective mono-cross-coupling of substrates with two identical halo groups is a useful method for synthesizing substituted monohalogenated arenes. Such arenes constitute an important class of compounds, which are commonly identified as drug components and synthetic intermediates. Traditionally, these site-selective reactions have been [...] Read more.
Pd-catalyzed, site-selective mono-cross-coupling of substrates with two identical halo groups is a useful method for synthesizing substituted monohalogenated arenes. Such arenes constitute an important class of compounds, which are commonly identified as drug components and synthetic intermediates. Traditionally, these site-selective reactions have been realized in a “substrate-controlled” manner, which is based on the steric and electronic differences between the two carbon-halogen bonds of the substrate. Recently, an alternative strategy, “catalyst-controlled” site-selective cross-coupling, has emerged. In this strategy, the preferred reaction site of a dihaloarene can be switched, merely by changing the catalyst used. This type of selective reaction further expands the utility of Pd-catalyzed cross-coupling. In this review, we summarize the reported examples of catalyst-controlled site-selectivity switching in Pd-catalyzed cross-coupling of dihaloarenes. Full article
(This article belongs to the Special Issue Palladium Catalysts for Cross-Coupling Reaction)
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719 KiB  
Review
Palladium-Catalyzed Intermolecular Oxidative Amination of Alkenes with Amines, Using Molecular Oxygen as Terminal Oxidant
by Yasushi Obora and Yasutaka Ishii
Catalysts 2013, 3(4), 794-810; https://doi.org/10.3390/catal3040794 - 16 Oct 2013
Cited by 28 | Viewed by 10315
Abstract
In this review, we summarize recent progress from our group with regard to Pd-catalyzed oxidative amination of alkenes with amines. Intermolecular oxidative amination of alkenes with secondary anilines was induced using a palladium-complex catalyst combined with molybdovanadophosphate as a co-catalyst under dioxygen, leading [...] Read more.
In this review, we summarize recent progress from our group with regard to Pd-catalyzed oxidative amination of alkenes with amines. Intermolecular oxidative amination of alkenes with secondary anilines was induced using a palladium-complex catalyst combined with molybdovanadophosphate as a co-catalyst under dioxygen, leading to allylic amines and enamines in good yields with high selectivities. The reaction proceeded efficiently, using molecular oxygen as the terminal oxidant. In addition, palladium-catalyzed oxidative amination of alkenes with anilines as primary amines was achieved using molecular oxygen as the sole oxidant, producing (Z)-N-alkenyl-substituted anilines in high yields. Full article
(This article belongs to the Special Issue Palladium Catalysts for Cross-Coupling Reaction)
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