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Molecules
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Transition Metal-Catalyzed Reactions in Heterocyclic Synthesis
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Transition Metal-Catalyzed Reactions in Heterocyclic Synthesis

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

Deadline for manuscript submissions: closed (31 December 2020) | Viewed by 10734

Special Issue Editors

Prof. Dr. Gerald Guillaumet

E-Mail Website
Guest Editor
Institute of Organic and Analytical Chemistry, Universite d'Orleans, UMR CNRS 7311, BP 6759, 45067 Orleans, CEDEX 2, France
Interests: heterocyclic chemistry; C–H functionalization; medicinal chemistry; drug discovery for CNS; metabolic and cardiovascular diseases; anticancer chemotherapy; chemical biology; organic synthesis
Prof. Dr. Saïd El Kazzouli

E-Mail Website
Guest Editor
Euromed Research Center, Euromed Institute of Technology, Euromed University of Fes, Route de Meknes, 30000 Fes, Morocco
Interests: organic synthesis; medicinal chemistry; heterocyclic chemistry; green chemistry; homogenious catalysis; dendrimers chemistry; C–H functionalization
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Transition metal-catalyzed reactions are very powerful tools in organic synthesis. The advances made in carbon–carbon bond formation have led to the functionalization of various heterocyclic systems, with important applications in pharmaceuticals, agrochemicals, and optoelectronic materials. Thanks to two main strategies with very high scientific significance in organic chemistry—namely, the classical methods of the metal-catalyzed cross-coupling reactions such as Suzuki-Miyaura, Heck, Sonogashira, Negishi, Stille, Kumada, Hyama and the recent methods of C-H functionalization including the direct arylation and alkenykation as well as the oxidative arylation and alkenylation. Review papers summarizing the most important achievement in the functionalization of specific heterocyclic systems, using either classical cross-coupling or new C-H activation methods would be very useful for the chemist community. In addition, original papers that address important issues in heterocyclic functionalization, using one or more of the reactions cited above would also be appreciated.

This Special Issue aims to cover recent advances in transition metal-catalyzed reactions, focusing on the two main strategies mentioned above and including reactions involving heterocyclic systems, with the formation of C–C bonds.

We invite research papers and reviews covering the above-mentioned topics.

Prof. Gerald Guillaumet
Prof. Saïd El Kazzouli
Guest Editors

Manuscript Submission Information

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. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short 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 thoroughly refereed through a single-blind 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 semimonthly 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 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • heterocycles
  • Suzuki-Miyaura
  • Heck
  • Sonogashira
  • Negishi
  • Stille
  • direct arylation
  • direct alkenylation
  • oxidative arylation
  • oxidative alkenylkation

Published Papers (3 papers)

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Research

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8 pages, 1240 KiB  
Article
Total Synthesis of Cyclopiamide A Using Palladium-Catalyzed Domino Cyclization
by Sunhwa Park, Kye Jung Shin and Jae Hong Seo
Molecules 2020, 25(21), 4903; https://doi.org/10.3390/molecules25214903 - 23 Oct 2020
Viewed by 2161
Abstract
Total synthesis of cyclopiamide A was accomplished using a palladium-catalyzed domino cyclization. Three rings in the tetracyclic skeleton of cyclopiamide A were constructed in a one-step domino reaction incorporating double carbopalladation and C-H activation. Full article
(This article belongs to the Special Issue Transition Metal-Catalyzed Reactions in Heterocyclic Synthesis)
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11 pages, 2216 KiB  
Article
“On Water” Palladium Catalyzed Direct Arylation of 1H-Indazole and 1H-7-Azaindazole
by Khadija Gambouz, Abdelmoula El Abbouchi, Sarah Nassiri, Franck Suzenet, Mostapha Bousmina, Mohamed Akssira, Gérald Guillaumet and Saïd El Kazzouli
Molecules 2020, 25(12), 2820; https://doi.org/10.3390/molecules25122820 - 18 Jun 2020
Cited by 11 | Viewed by 3391
Abstract
The C3 direct arylation of 1H-indazole and 1H-7-azaindazole has been a significant challenge due to the lack of the reactivity at this position. In this paper, we describe a mild and an efficient synthesis of new series of C3-aryled [...] Read more.
The C3 direct arylation of 1H-indazole and 1H-7-azaindazole has been a significant challenge due to the lack of the reactivity at this position. In this paper, we describe a mild and an efficient synthesis of new series of C3-aryled 1H-indazoles and C3-aryled 1H-7-azaindazoles via a C3 direct arylation using water as solvent. On water, PPh3 was effective as a ligand along with a lower charge of the catalyst Pd(OAc)2 (5 mol%) at 100 °C, leading to C3-aryled 1H-indazoles or C3-aryled 1H-7-azaindazoles in moderate to good yields. Full article
(This article belongs to the Special Issue Transition Metal-Catalyzed Reactions in Heterocyclic Synthesis)
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Review

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27 pages, 6435 KiB  
Review
Discovery, Synthesis, and Scale-up of Efficient Palladium Catalysts Useful for the Modification of Nucleosides and Heteroarenes
by Shatrughn Bhilare, Harshita Shet, Yogesh S. Sanghvi and Anant R. Kapdi
Molecules 2020, 25(7), 1645; https://doi.org/10.3390/molecules25071645 - 3 Apr 2020
Cited by 14 | Viewed by 4715
Abstract
Nucleic acid derivatives are imperative biomolecules and are involved in life governing processes. The chemical modification of nucleic acid is a fascinating area for researchers due to the potential activity exhibited as antiviral and antitumor agents. In addition, these molecules are also of [...] Read more.
Nucleic acid derivatives are imperative biomolecules and are involved in life governing processes. The chemical modification of nucleic acid is a fascinating area for researchers due to the potential activity exhibited as antiviral and antitumor agents. In addition, these molecules are also of interest toward conducting useful biochemical, pharmaceutical, and mutagenic study. For accessing such synthetically useful structures and features, transition-metal catalyzed processes have been proven over the years to be an excellent tool for carrying out the various transformations with ease and under mild reaction conditions. Amidst various transition-metal catalyzed processes available for nucleoside modification, Pd-catalyzed cross-coupling reactions have proven to be perhaps the most efficient, successful, and broadly applicable reactions in both academia and industry. Pd-catalyzed C–C and C–heteroatom bond forming reactions have been widely used for the modification of the heterocyclic moiety in the nucleosides, although a single catalyst system that could address all the different requirements for nucleoside modifications isvery rare or non-existent. With this in mind, we present herein a review showcasing the recent developments and improvements from our research groups toward the development of Pd-catalyzed strategies including drug synthesis using a single efficient catalyst system for the modification of nucleosides and other heterocycles. The review also highlights the improvement in conditions or the yield of various bio-active nucleosides or commercial drugs possessing the nucleoside structural core. Scale ups wherever performed (up to 100 g) of molecules of commercial importance have also been disclosed. Full article
(This article belongs to the Special Issue Transition Metal-Catalyzed Reactions in Heterocyclic Synthesis)
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