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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 5370

Special Issue Editor


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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

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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

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Published Papers (2 papers)

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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 1251
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
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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 3390
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
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