Special Issue "Palladium Catalysts for Cross-Coupling Reaction"


A special issue of Catalysts (ISSN 2073-4344).

Deadline for manuscript submissions: closed (15 June 2014)

Special Issue Editor

Guest Editor
Prof. Dr. Kei Manabe
University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan
Website: http://w3pharm.u-shizuoka-ken.ac.jp/~yakka/English/profileManabe.html
E-Mail: manabe@u-shizuoka-ken.ac.jp
Interests: cross coupling; palladium catalyst; homogeneous/heterogeneous catalyst; selective reaction; allylic substitution; carbonylation; C-H activation; reaction mechanism; organometallic chemistry

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


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.

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

Published Papers (4 papers)

by  and
Catalysts 2014, 4(3), 307-320; doi:10.3390/catal4030307
Received: 29 May 2014; in revised form: 28 July 2014 / Accepted: 5 August 2014 / Published: 20 August 2014
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abstract graphic

by , ,  and
Catalysts 2013, 3(4), 839-852; doi:10.3390/catal3040839
Received: 9 August 2013; in revised form: 25 September 2013 / Accepted: 8 October 2013 / Published: 22 October 2013
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by  and
Catalysts 2013, 3(4), 794-810; doi:10.3390/catal3040794
Received: 25 July 2013; in revised form: 29 September 2013 / Accepted: 8 October 2013 / Published: 16 October 2013
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by , ,  and
Catalysts 2013, 3(2), 486-500; doi:10.3390/catal3020486
Received: 27 March 2013; in revised form: 9 May 2013 / Accepted: 10 May 2013 / Published: 16 May 2013
Show/Hide Abstract | Cited by 6 | PDF Full-text (408 KB) | HTML Full-text | XML Full-text | Supplementary Files
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Planned Papers

The below list represents only planned manuscripts. Some of these manuscripts have not been received by the Editorial Office yet. Papers submitted to MDPI journals are subject to peer-review.

Type of Paper: Article
Title: Palladium-Catalyzed Synthesis of Pentafluorophenyl-Substituted Porphyins
Author: Toshikatsu Takanami
Affiliation: Meiji Pharmaceutical University, Japan
Abstract: An efficient direct introduction of perfluoroaromatic substituents, such as pentafluorophenyl group, to porphyrin core utilizing palladium-catalyzed cross-coupling reaction of brominated porphyrins with bis(penta¬ fluoro¬ phenyl)¬zinc will be described in the planning paper. It is well-known that the chemical, physical, and biological properties of porphyrins can be systematically regulated by the electronic, steric, and conformational environments of their peripheral substituents as well as the central metal ions. Pentafluorophenyl and related perfluoroaromatic groups are expected to greatly affect the electronic properties of porphyrin core. Only a few methods, however, have been available for the preparation of porphyrins bearing perfluoroaromatic groups. Most popular and classic approach to these fluorinated porphyrins involves multiple condensation reactions of the appropriate aldehyde(s) with various monopyrroles or substituted dipyrromethanes under acidic conditions, followed by oxidation of resulting porphyrinogen intermediates. Despite significant improvements with the introduction of new reaction conditions, these multiple condensation methods still suffer from low yields, significant side products, and tedious purification, thereby restraining efficient preparation of porphyrin derivatives bearing perfluoroaromatic groups. Thus, the development of an alternative approach to porphyrins bearing perfluoroaromatic groups with higher simplicity, generality, and practicality remains an important goal. To achieve this goal, we have developed a palladium-catalyzed coupling reaction of brominated porphyrins with bis(perfluorophenyl)Zn reagents, the method being a new and straightforward access to porphyrin derivatives bearing perfluoroaromatic groups. The details of these approaches we have developed will be described in the planning paper.

Title: Catalyst-Controlled Site-Selectivity Switch in Pd-Catalyzed Cross-Coupling of Dihaloarenes
Kei Manabe* and Miyuki Yamaguchi
School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan
Pd-catalyzed cross-coupling reactions of haloarenes with organometallic reagents constitute one of the most important and practical transformations using transition metal-catalysts. Among them, site-selective mono-cross-coupling of substrates having two identical halo groups is a useful method for synthesizing substituted monohalogenated arenes, which constitute an important class of compounds common 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 difference of the two carbon‒halogen bonds of the substrates. Recently, an alternative strategy, “catalyst-controlled” site-selective cross-coupling, has emerged. In this strategy, the preferred reaction site of dihaloarenes can be switched merely by changing the catalyst used. This type of selective reactions further expands the utility of Pd-catalyzed cross-coupling. In this review, we summarize the reported examples of catalyst-controlled site-selectivity switch in Pd-catalyzed cross-coupling of dihaloarenes.

Title: Palladium on carbon-catalyzed Suzuki-Miyaura coupling reaction by the use of efficient and continuous flow system
Tomohiro Hattori, Aya Tsubone, Yoshinari Sawama, Yasunari Monguchi, Hironao Sajik
Laboratory of Gifu Pharmaceutical University, Gifu, Japan
The continuous flow Suzuki-Miyaura reaction between various haloarenes and aryl boronic acids was successfully achieved within only ca. 20 seconds during the passage into the cartridge filled with palladium on carbon (Pd/C). The palladium leaching never detected in the recovered reaction mixture by ICP-AES and the catalyst cartridge could be reused at least 200 times without degradation. The distinctive feature would make the method of practical use.

Last update: 12 August 2014

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