molecules-logo

Journal Browser

Journal Browser

The Suzuki–Miyaura Reaction: Exciting New Discoveries and Applications

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

Deadline for manuscript submissions: closed (31 July 2023) | Viewed by 5736

Special Issue Editor


E-Mail Website
Guest Editor
Department of Chemistry, University of North Florida, Jacksonville, FL 32224, USA
Interests: synthesis and catalysis in ionic liquids; synthetic method development; cross-coupling reactions; carbocation and onium ion chemistry; stable ion chemistry; synthesis of small molecule building blocks; organofluorine chemistry; heteroatom chemistry with emphasis on P and Si

Special Issue Information

Dear Colleagues,

The Suzuki–Miyaura (SM) cross-coupling reaction continues to have a profound influence on advancing organic chemistry in its broadest sense, and the progress in this area, especially during the past decade, has been nothing short of astonishing. The SM reaction is widely utilized in the synthesis of pharmaceuticals, smart materials and complex natural and unnatural compounds.

Recent efforts focusing on the development of novel homogeneous and heterogeneous catalysts and new ligands for C-C and C-X cross-coupling have resulted in increased efficiency, higher yields, and enantioselectivity. Other studies aimed at the discovery of new coupling partners, applications of neoteric and green media such as ionic liquids and deep eutectic solvents, and the development of new experimental designs employing flow chemistry, multicomponent and sequential reactions have greatly expanded the utility and scope of the SM reaction. Unraveling the intricate mechanistic aspects of this transformation, both experimentally and computationally, continues to be an integral part of the recent progress in this dynamic area.

The goal of this Special Issue is to provide a forum for active scientists and researchers in the field to present their studies focusing on the latest discoveries and trends. The Issue welcomes original research papers as well as timely reviews.

Professor Kenneth Laali
Guest Editor

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

  • Suzuki–Miyaura reaction
  • C-C and C-heteroatom cross-coupling
  • catalysts and ligands
  • coupling partners
  • mechanistic insights
  • experimental designs
  • neoteric and green media
  • asymmetric synthesis
  • synthetic applications

Benefits of Publishing in a Special Issue

  • Ease of navigation: Grouping papers by topic helps scholars navigate broad scope journals more efficiently.
  • Greater discoverability: Special Issues support the reach and impact of scientific research. Articles in Special Issues are more discoverable and cited more frequently.
  • Expansion of research network: Special Issues facilitate connections among authors, fostering scientific collaborations.
  • External promotion: Articles in Special Issues are often promoted through the journal's social media, increasing their visibility.
  • e-Book format: Special Issues with more than 10 articles can be published as dedicated e-books, ensuring wide and rapid dissemination.

Further information on MDPI's Special Issue polices can be found here.

Published Papers (2 papers)

Order results
Result details
Select all
Export citation of selected articles as:

Research

10 pages, 583 KiB  
Article
Scalable Synthesis of TRPV1 Antagonist Bipyridinyl Benzimidazole Derivative via the Suzuki–Miyaura Reaction and Selective SeO2 Oxidation
by Joon-Hwan Lee, Jiduck Kim and Hakwon Kim
Molecules 2023, 28(2), 836; https://doi.org/10.3390/molecules28020836 - 13 Jan 2023
Viewed by 1352
Abstract
In this study, a kilogram-scale synthesis of a potent TRPV1 antagonist, 1, is described. To synthesize bipyridinyl benzimidazole derivative 1, we have developed a scalable Suzuki–Miyaura reaction capable of providing a key intermediate, 6′-methyl-3-(trifluoromethyl)-2,3′-bipyridine 4, on a kilogram scale. Then, unlike [...] Read more.
In this study, a kilogram-scale synthesis of a potent TRPV1 antagonist, 1, is described. To synthesize bipyridinyl benzimidazole derivative 1, we have developed a scalable Suzuki–Miyaura reaction capable of providing a key intermediate, 6′-methyl-3-(trifluoromethyl)-2,3′-bipyridine 4, on a kilogram scale. Then, unlike the existing oxidation reaction pathway, two synthetic routes that can be applied to mass production of bipyridinyl carboxylic acid intermediate 5 or aldehyde intermediate 6 were developed by appropriately controlling the oxidation reaction using a selenium dioxide oxidizing agent. Using our developed synthetic procedure, which includes Suzuki–Miyaura coupling, selective selenium dioxide oxidation, and benzimidazole formation, multi-kilogram-scale bi-pyridinyl benzimidazole derivative 1 can be synthesized. Full article
Show Figures

Scheme 1

15 pages, 7153 KiB  
Article
Preparation of Synthetic and Natural Derivatives of Flavonoids Using Suzuki–Miyaura Cross-Coupling Reaction
by Martina Hurtová, David Biedermann, Zuzana Osifová, Josef Cvačka, Kateřina Valentová and Vladimír Křen
Molecules 2022, 27(3), 967; https://doi.org/10.3390/molecules27030967 - 31 Jan 2022
Cited by 9 | Viewed by 3620
Abstract
Herein, we report the use of the Suzuki–Miyaura cross-coupling reaction for the preparation of a library of synthetic derivatives of flavonoids for biological activity assays. We have investigated the reactivity of halogenated flavonoids with aryl boronates and with boronyl flavonoids. This reaction was [...] Read more.
Herein, we report the use of the Suzuki–Miyaura cross-coupling reaction for the preparation of a library of synthetic derivatives of flavonoids for biological activity assays. We have investigated the reactivity of halogenated flavonoids with aryl boronates and with boronyl flavonoids. This reaction was used to prepare new synthetic derivatives of flavonoids substituted at C-8 with aryl, heteroaryl, alkyl, and boronate substituents. The formation of flavonoid boronate enabled a cross-coupling reaction with halogenated flavones yielding biflavonoids connected at C-8. This method was used for the preparation of natural compounds including C-8 prenylated compounds, such as sinoflavonoid NB. Flavonoid boronates were used for the preparation of rare C-8 hydroxyflavonoids (natural flavonoids gossypetin and hypolaetin). A series of previously unknown derivatives of quercetin and luteolin were prepared and fully characterized. Full article
Show Figures

Graphical abstract

Back to TopTop