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Synthesis and Application of Organoboron Derivatives
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Synthesis and Application of Organoboron Derivatives

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

Deadline for manuscript submissions: closed (28 February 2021) | Viewed by 23405

Special Issue Editor

Dr. Laurent Chabaud

E-Mail Website
Guest Editor
Institute of Molecular Sciences, CNRS, Université de Bordeaux, 351 Cours de la Libération, 33405 Talence, CEDEX, France
Interests: organic chemistry; organometallic chemistry; boron chemistry; catalysis; C–H functionalization; atropisomers; polymers

Special Issue Information

Dear Colleagues,

The chemistry of organoboron derivatives is recognized as a mainstay in modern organic synthesis. The great value of these reagents has been widely demonstrated in the formation of carbon–carbon or carbon–heteroatom bonds. Beyond their common use as intermediates in organic chemistry, the singular properties of the boron atom in organoboron derivatives can be exploited for a number of applications. These range from material to medical science and include polymers, sensors, luminescent or bioactive compounds, and many more.

This Special Issue aims to present recent advances in organoboron chemistry, from the development of new synthetic methods, the study of their properties (electronic, optical, biological, etc.), to their use in a broad range of fields, including materials, medicinal chemistry, analytical chemistry, etc.

We welcome communications, full research articles, and reviews on topics related to these fields.

Dr. Laurent Chabaud
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.

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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

  • Organoboron compounds
  • B-heterocycles
  • New synthetic methods
  • Catalysis
  • Cross-coupling reactions
  • Radical reactions
  • Materials
  • Polymers
  • Medicinal chemistry
  • Optical properties
  • Imaging
  • Chemosensors

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Published Papers (7 papers)

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Research

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15 pages, 5858 KiB  
Article
Copper-Catalyzed Ring-Opening Reactions of Alkyl Aziridines with B2pin2: Experimental and Computational Studies
by Lucilla Favero, Andrea Menichetti, Cosimo Boldrini, Lucrezia Margherita Comparini, Valeria Di Bussolo, Sebastiano Di Pietro and Mauro Pineschi
Molecules 2021, 26(23), 7399; https://doi.org/10.3390/molecules26237399 - 6 Dec 2021
Cited by 2 | Viewed by 2943
Abstract
The possibility to form new C–B bonds with aziridines using diboron derivatives continues to be a particularly challenging field in view of the direct preparation of functionalized β-aminoboronates, which are important compounds in drug discovery, being a bioisostere of β-aminoacids. We now report [...] Read more.
The possibility to form new C–B bonds with aziridines using diboron derivatives continues to be a particularly challenging field in view of the direct preparation of functionalized β-aminoboronates, which are important compounds in drug discovery, being a bioisostere of β-aminoacids. We now report experimental and computational data that allows the individuation of the structural requisites and of reaction conditions necessary to open alkyl aziridines using bis(pinacolate)diboron (B2pin2) in a regioselective nucleophilic addition reaction under copper catalysis. Full article
(This article belongs to the Special Issue Synthesis and Application of Organoboron Derivatives)
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14 pages, 5195 KiB  
Article
Towards Enhanced MRI Performance of Tumor-Specific Dimeric Phenylboronic Contrast Agents
by Jonathan Martinelli, Lorenzo Tei, Simonetta Geninatti Crich, Diego Alberti and Kristina Djanashvili
Molecules 2021, 26(6), 1730; https://doi.org/10.3390/molecules26061730 - 19 Mar 2021
Cited by 5 | Viewed by 2571
Abstract
It is known that phenylboronic acid (PBA) can target tumor tissues by binding to sialic acid, a substrate overexpressed by cancer cells. This capability has previously been explored in the design of targeting diagnostic probes such as Gd- and 68Ga-DOTA-EN-PBA, two contrast [...] Read more.
It is known that phenylboronic acid (PBA) can target tumor tissues by binding to sialic acid, a substrate overexpressed by cancer cells. This capability has previously been explored in the design of targeting diagnostic probes such as Gd- and 68Ga-DOTA-EN-PBA, two contrast agents for magnetic resonance imaging (MRI) and positron emission tomography (PET), respectively, whose potential has already been demonstrated through in vivo experiments. In addition to its high resolution, the intrinsic low sensitivity of MRI stimulates the search for more effective contrast agents, which, in the case of small-molecular probes, basically narrows down to either increased tumbling time of the entire molecule or elevated local concentration of the paramagnetic ions, both strategies resulting in enhanced relaxivity, and consequently, a higher MRI contrast. The latter strategy can be achieved by the design of multimeric GdIII complexes. Based on the monomeric PBA-containing probes described recently, herein, we report the synthesis and characterization of the dimeric analogues (GdIII-DOTA-EN)2-PBA and (GdIII-DOTA-EN)2F2PBA. The presence of two Gd ions in one molecule clearly contributes to the improved biological performance, as demonstrated by the relaxometric study and cell-binding investigations. Full article
(This article belongs to the Special Issue Synthesis and Application of Organoboron Derivatives)
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13 pages, 4458 KiB  
Article
Synthesis of Bis(Carboranyl)amides 1,1′-μ-(CH2NH(O)C(CH2)n-1,2-C2B10H11)2 (n = 0, 1) and Attempt of Synthesis of Gadolinium Bis(Dicarbollide)
by Yasunobu Asawa, Aleksandra V. Arsent’eva, Sergey A. Anufriev, Alexei A. Anisimov, Kyrill Yu. Suponitsky, Oleg A. Filippov, Hiroyuki Nakamura and Igor B. Sivaev
Molecules 2021, 26(5), 1321; https://doi.org/10.3390/molecules26051321 - 2 Mar 2021
Cited by 1 | Viewed by 2849
Abstract
Bis(carboranyl)amides 1,1′-μ-(CH2NH(O)C(CH2)n-1,2-C2B10H11)2 (n = 0, 1) were prepared by the reactions of the corresponding carboranyl acyl chlorides with ethylenediamine. Crystal molecular structure of 1,1′-μ-(CH2NH(O)C-1,2-C2B10 [...] Read more.
Bis(carboranyl)amides 1,1′-μ-(CH2NH(O)C(CH2)n-1,2-C2B10H11)2 (n = 0, 1) were prepared by the reactions of the corresponding carboranyl acyl chlorides with ethylenediamine. Crystal molecular structure of 1,1′-μ-(CH2NH(O)C-1,2-C2B10H11)2 was determined by single crystal X-ray diffraction. Treatment of bis(carboranyl)amides 1,1′-μ-(CH2NH(O)C(CH2)n-1,2-C2B10H11)2 with ammonium or cesium fluoride results in partial deboronation of the ortho-carborane cages to the nido-carborane ones with formation of [7,7′(8′)-μ-(CH2NH(O)C(CH2)n-7,8-C2B9H11)2]2−. The attempted reaction of [7,7′(8′)-μ-(CH2NH(O)CCH2-7,8-C2B9H11)2]2− with GdCl3 in 1,2-dimethoxy- ethane did not give the expected metallacarborane. The stability of different conformations of Gd-containing metallacarboranes has been estimated by quantum-chemical calculations using [3,3-μ-DME-3,3′-Gd(1,2-C2B9H11)2]− as a model. It was found that in the most stable conformation the CH groups of the dicarbollide ligands are in anti,anti-orientation with respect to the DME ligand, while any rotation of the dicarbollide ligand reduces the stability of the system. This makes it possible to rationalize the design of carborane ligands for the synthesis of gadolinium metallacarboranes on their base. Full article
(This article belongs to the Special Issue Synthesis and Application of Organoboron Derivatives)
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13 pages, 2257 KiB  
Article
Synthesis and Influence of 3-Amino Benzoxaboroles Structure on Their Activity against Candida albicans
by Dorota Wieczorek, Ewa Kaczorowska, Marta Wiśniewska, Izabela D. Madura, Magdalena Leśniak, Jacek Lipok and Agnieszka Adamczyk-Woźniak
Molecules 2020, 25(24), 5999; https://doi.org/10.3390/molecules25245999 - 18 Dec 2020
Cited by 6 | Viewed by 2372
Abstract
Benzoxaboroles emerged recently as molecules of high medicinal potential with Kerydin® (Tavaborole) and Eucrisa® (Crisaborole) currently in clinical practice as antifungal and anti-inflammatory drugs, respectively. Over a dozen of 3-amino benzoxaboroles, including Tavaborole’s derivatives, have been synthetized and characterized in terms [...] Read more.
Benzoxaboroles emerged recently as molecules of high medicinal potential with Kerydin® (Tavaborole) and Eucrisa® (Crisaborole) currently in clinical practice as antifungal and anti-inflammatory drugs, respectively. Over a dozen of 3-amino benzoxaboroles, including Tavaborole’s derivatives, have been synthetized and characterized in terms of their activity against Candida albicans as a model pathogenic fungus. The studied compounds broaden considerably the structural diversity of reported benzoxaboroles, enabling determination of the influence of the introduction of a heterocyclic amine, a fluorine substituent as well as the formyl group on antifungal activity of those compounds. The determined zones of the growth inhibition of examined microorganism indicate high diffusion of majority of the studied compounds within the applied media as well as their reasonable activity. The Minimum Inhibitory Concentration (MIC) values show that the introduction of an amine substituent in position “3” of the benzoxaborole heterocyclic ring results in a considerable drop in activity in comparison with Tavaborole (AN2690) as well as unsubstituted benzoxaborole (AN2679). In all studied cases the presence of a fluorine substituent at position para to the boron atom results in lower MIC values (higher activity). Interestingly, introduction of a fluorine substituent in the more distant piperazine phenyl ring does not influence MIC values. As determined by X-ray studies, introduction of a formyl group in proximity of the boron atom results in a considerable change of the boronic group geometry. The presence of a formyl group next to the benzoxaborole unit is also detrimental for activity against Candida albicans. Full article
(This article belongs to the Special Issue Synthesis and Application of Organoboron Derivatives)
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12 pages, 2117 KiB  
Article
Synthesis, Molecular Docking, and In Vitro Boron Neutron Capture Therapy Assay of Carboranyl Sinomenine
by Jianghong Cai, Narayan S. Hosmane, Masao Takagaki and Yinghuai Zhu
Molecules 2020, 25(20), 4697; https://doi.org/10.3390/molecules25204697 - 14 Oct 2020
Cited by 6 | Viewed by 2787
Abstract
In comparison with pristine sinomenine and carborane precursors, the calculations of molecular docking with matrix metalloproteinases (MMPs) and methylcarboranyl-n-butyl sinomenine showed improved interactions. Accordingly, methylcarboranyl-n-butyl sinomenine shows a high potential in the treatment of rheumatoid arthritis (RA) in the [...] Read more.
In comparison with pristine sinomenine and carborane precursors, the calculations of molecular docking with matrix metalloproteinases (MMPs) and methylcarboranyl-n-butyl sinomenine showed improved interactions. Accordingly, methylcarboranyl-n-butyl sinomenine shows a high potential in the treatment of rheumatoid arthritis (RA) in the presence of slow neutrons. The reaction of potassium salt of sinomenie, which is generated from the deprotonation of sinomenine (1) using potassium carbonate in a solvent of N,N-dimethyl formamide, with 4-methylcarboranyl-n-butyl iodide, (2) forms methylcarboranyl-n-butyl sinomenine (3) in 54.3% yield as a new product. This new compound was characterized by 1H, 13C, and 11B NMR spectroscopy, FT-IR spectroscopy, and elemental analyses to confirm its molecular composition. In addition to molecular docking interactions with MMPs, the in vitro killing effects of 3, along with its toxicity measurements, exhibited its potential to be the new drug delivery agent for boron neutron capture synovectomy (BNCS) and boron neutron capture therapy (BNCT) for the treatment of rheumatoid arthritis (RA) and cancers in the presence of slow neutrons, respectively. Full article
(This article belongs to the Special Issue Synthesis and Application of Organoboron Derivatives)
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Review

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41 pages, 12961 KiB  
Review
Recent Advances in the Synthesis of Borinic Acid Derivatives
by Marion Boyet, Laurent Chabaud and Mathieu Pucheault
Molecules 2023, 28(6), 2660; https://doi.org/10.3390/molecules28062660 - 15 Mar 2023
Cited by 2 | Viewed by 5660
Abstract
Borinic acids [R2B(OH)] and their chelate derivatives are a subclass of organoborane compounds used in cross-coupling reactions, catalysis, medicinal chemistry, polymer or optoelectronics materials. In this paper, we review the recent advances in the synthesis of diarylborinic acids and their four-coordinated [...] Read more.
Borinic acids [R2B(OH)] and their chelate derivatives are a subclass of organoborane compounds used in cross-coupling reactions, catalysis, medicinal chemistry, polymer or optoelectronics materials. In this paper, we review the recent advances in the synthesis of diarylborinic acids and their four-coordinated analogs. The main strategies to build up borinic acids rely either on the addition of organometallic reagents to boranes (B(OR)3, BX3, aminoborane, arylboronic esters) or the reaction of triarylboranes with a ligand (diol, amino alcohol, etc.). After general practical considerations of borinic acids, an overview of the main synthetic methods, their scope and limitations is provided. We also discuss some mechanistic aspects. Full article
(This article belongs to the Special Issue Synthesis and Application of Organoboron Derivatives)
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21 pages, 14204 KiB  
Review
Recent Progress on Synthesis of N,N′-Chelate Organoboron Derivatives
by Tianbao Yang, Niu Tang, Qizhong Wan, Shuang-Feng Yin and Renhua Qiu
Molecules 2021, 26(5), 1401; https://doi.org/10.3390/molecules26051401 - 5 Mar 2021
Cited by 6 | Viewed by 3279
Abstract
N,N′-chelate organoboron compounds have been successfully applied in bioimaging, organic light-emitting diodes (OLEDs), functional polymer, photocatalyst, electroluminescent (EL) devices, and other science and technology areas. However, the concise and efficient synthetic methods become more and more significant for material science, [...] Read more.
N,N′-chelate organoboron compounds have been successfully applied in bioimaging, organic light-emitting diodes (OLEDs), functional polymer, photocatalyst, electroluminescent (EL) devices, and other science and technology areas. However, the concise and efficient synthetic methods become more and more significant for material science, biomedical research, or other practical science. Here, we summarized the organoboron-N,N′-chelate derivatives and showed the different routes of their syntheses. Traditional methods to synthesize N,N′-chelate organoboron compounds were mainly using bidentate ligand containing nitrogen reacting with trivalent boron reagents. In this review, we described a series of bidentate ligands, such as bipyridine, 2-(pyridin-2-yl)-1H-indole, 2-(5-methyl-1H-pyrrol-2-yl)quinoline, N-(quinolin-8-yl)acetamide, 1,10-phenanthroline, and diketopyrrolopyrrole (DPP). Full article
(This article belongs to the Special Issue Synthesis and Application of Organoboron Derivatives)
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