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Recent Advances in Boron Chemistry
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Recent Advances in Boron Chemistry

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

Deadline for manuscript submissions: closed (15 March 2015) | Viewed by 50904

Special Issue Editor

Prof. Dr. John Spencer

E-Mail Website
Guest Editor
Department of Chemistry, University of Sussex, Sussex, UK
Interests: palladium catalysis; medicinal chemistry; heterocycle synthesis; cancer; p53
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Boron chemistry is very important in both an academic and technological sense. There has been a huge investment in materials science and inorganic chemistry behind boron and, consequently, it has applications in everyday use in, e.g., bleaches, glasses, detergents, abrasives, magnets, etc. Notably, the synthetic organic chemistry of boron is extensive, for example:

  • Suzuki-Miyaura couplings are powerful C-C bond forming reactions vital in organic and medicinal chemistry;
  • C-H activation chemistry combines atom economical borylations with a number of potential in situ modifications;
  • Matteson homologations are essential for the synthesis of a number of chiral boron compounds, especially ones with good biological activity

not to mention, but not limited to, hydroborylation chemistry, Chan-Lam couplings, MIDA chemistry, Lewis Acid mediated reactions. Boron plays an increasingly important role in chemical biology, medicinal chemistry and in Nature, e.g., AI-2 and boromycin. One can think of sensors, boron neutron capture therapy and small-molecule boron-based drugs such as oxaboroles and Velcade, a marketed boronic acid, used for cancer therapy.

It is for these reasons that you are cordially invited to participate in this special edition dedicated to boron chemistry. Contributions in organic synthesis, sensors, medicinal, natural products, materials science and inorganic chemistry of boron are invited.

Dr. John Spencer
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

  • boron in organic synthesis
  • Suzuki couplings
  • boron-based druglike molecules
  • organoboron chemistry
  • boron-based sensors
  • boron-based Lewis Acid chemistry

Published Papers (6 papers)

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Research

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884 KiB  
Article
Cytotoxicity of the Urokinase-Plasminogen Activator Inhibitor Carbamimidothioic Acid (4-Boronophenyl) Methyl Ester Hydrobromide (BC-11) on Triple-Negative MDA-MB231 Breast Cancer Cells
by Alessandra Longo, Mariangela Librizzi, Irina S. Chuckowree, Christine B. Baltus, John Spencer and Claudio Luparello
Molecules 2015, 20(6), 9879-9889; https://doi.org/10.3390/molecules20069879 - 28 May 2015
Cited by 7 | Viewed by 6468
Abstract
BC-11 is an easily synthesized simple thiouronium-substituted phenylboronic acid, which has been shown to be cytotoxic on triple negative MDA-MB231 breast cancer cells by inducing a perturbation of cell cycle when administered at a concentration equal to its ED50 at 72 h [...] Read more.
BC-11 is an easily synthesized simple thiouronium-substituted phenylboronic acid, which has been shown to be cytotoxic on triple negative MDA-MB231 breast cancer cells by inducing a perturbation of cell cycle when administered at a concentration equal to its ED50 at 72 h (117 μM). Exposure of cells to BC-11, either pre-absorbed with a soluble preparation of the N-terminal fragment of urokinase-plasminogen activator (uPa), or in co-treatment with two different EGFR inhibitors, indicated that: (i) BC-11 acts via binding to the N-terminus of the enzyme where uPa- and EGF receptor-recognizing sites are present, thereby abrogating the growth-sustaining effect resulting from receptor binding; and (ii) the co-presence of the EGFR inhibitor PD153035 potentiates BC-11’s cytotoxicity. Exposure of cells to a higher concentration of BC-11 corresponding to its ED75 at 72 h (250 μM) caused additional impairment of mitochondrial activity, the production of reactive oxygen species and promotion of apoptosis. Therefore, BC-11 treatment appears to show potential for the development of this class of compounds in the prevention and/or therapy of “aggressive” breast carcinoma. Full article
(This article belongs to the Special Issue Recent Advances in Boron Chemistry)
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1353 KiB  
Article
Synthesis and 11C-Radiolabelling of 2-Carboranyl Benzothiazoles
by Kiran B. Gona, Jaya Lakshmi V. N. P. Thota, Zuriñe Baz, Vanessa Gómez-Vallejo and Jordi Llop
Molecules 2015, 20(5), 7495-7508; https://doi.org/10.3390/molecules20057495 - 23 Apr 2015
Cited by 8 | Viewed by 5713
Abstract
Dicarba-closo-dodecaboranes, commonly known as carboranes, possess unique physico-chemical properties and can be used as hydrophobic moieties during the design of new drugs or radiotracers. In this work, we report the synthesis of two analogues of 2-(4-aminophenyl)benzothiazole (a compound that was found [...] Read more.
Dicarba-closo-dodecaboranes, commonly known as carboranes, possess unique physico-chemical properties and can be used as hydrophobic moieties during the design of new drugs or radiotracers. In this work, we report the synthesis of two analogues of 2-(4-aminophenyl)benzothiazole (a compound that was found to elicit pronounced inhibitory effects against certain breast cancer cell lines in vitro) in which the phenyl ring has been substituted by a m-carborane cage. Two different synthetic strategies have been used. For the preparation of 1-(9-amino-1,7-dicarba-closo-dodecaboran-1-yl)-benzo-thiazole, the benzothiazole group was first introduced on one of the cluster carbon atoms of m-carborane and the amine group was further attached in three steps. For the synthesis of 1-(9-amino-1,7-dicarba-closo-dodecaboran-1-yl)-6-hydroxybenzothiazole, iodination was performed before introducing the benzothiazole group, and the amino group was subsequently introduced in six steps. Both compounds were radiolabelled with carbon-11 using [11C]CH3OTf as the labelling agent. Radiolabelling yields and radiochemical purities achieved should enable subsequent in vitro and in vivo investigations. Full article
(This article belongs to the Special Issue Recent Advances in Boron Chemistry)
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748 KiB  
Article
Trans-Selective Rhodium Catalysed Conjugate Addition of Organoboron Reagents to Dihydropyranones
by Hannah J. Edwards, Sean Goggins and Christopher G. Frost
Molecules 2015, 20(4), 6153-6166; https://doi.org/10.3390/molecules20046153 - 08 Apr 2015
Cited by 3 | Viewed by 5890
Abstract
The selective synthesis of 2,6-trans-tetrahydropyran derivatives employing the rhodium catalysed addition of organoboron reagents to dihydropyranone templates, derived from a zinc-catalysed hetero-Diels-Alder reaction, is reported. The addition of both arylboronic acids and potassium alkenyltrifluoroborates have been accomplished in high yields using [...] Read more.
The selective synthesis of 2,6-trans-tetrahydropyran derivatives employing the rhodium catalysed addition of organoboron reagents to dihydropyranone templates, derived from a zinc-catalysed hetero-Diels-Alder reaction, is reported. The addition of both arylboronic acids and potassium alkenyltrifluoroborates have been accomplished in high yields using commercially-available [Rh(cod)(OH)]2 catalyst. The selective formation of the 2,6-trans-tetrahydropyran stereoisomer is consistent with a mechanism involving alkene association and carbometalation on the less hindered face of the dihydropyranone. Full article
(This article belongs to the Special Issue Recent Advances in Boron Chemistry)
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1515 KiB  
Communication
σ- versus π-Activation of Alkynyl Benzoates Using B(C6F5)3
by Alexander Bähr, Lewis C. Wilkins, Kevin Ollegott, Benson M. Kariuki and Rebecca L. Melen
Molecules 2015, 20(3), 4530-4547; https://doi.org/10.3390/molecules20034530 - 12 Mar 2015
Cited by 9 | Viewed by 7756
Abstract
We have prepared a range of alkynyl benzoates in high yields and have investigated their reactivities with the strong Lewis acid B(C6F5)3. In such molecules both σ-activation of the carbonyl and π-activation of the alkyne are possible. [...] Read more.
We have prepared a range of alkynyl benzoates in high yields and have investigated their reactivities with the strong Lewis acid B(C6F5)3. In such molecules both σ-activation of the carbonyl and π-activation of the alkyne are possible. In contrast to the reactivity of propargyl esters with B(C6F5)3 which proceed via 1,2-addition of the ester and B(C6F5)3 across the alkyne, the inclusion of an additional CH2 spacer switches off the intramolecular cyclization and selective σ-activation of the carbonyl group is observed through adduct formation. This change in reactivity appears due to the instability of the species which would be formed through B(C6F5)3 activation of the alkyne. Full article
(This article belongs to the Special Issue Recent Advances in Boron Chemistry)
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741 KiB  
Article
Synthesis, Characterisation and Reactions of Phosphine-Substituted Alkynylboronates and Alkynyltrifluoroborate Salts
by Jérôme F. Vivat, Sylvestre P. J. T. Bachollet, Harry Adams and Joseph P. A. Harrity
Molecules 2014, 19(12), 21324-21334; https://doi.org/10.3390/molecules191221324 - 18 Dec 2014
Viewed by 5634
Abstract
The synthesis and structural characterisation of phosphine-substituted alkynylboronates is reported. A P(III)-centred alkynylboronate (2) was prepared that showed little evidence for the conjugation of the P-lone pair to the boron via the alkyne π-system, as judged by X-ray crystallography studies of [...] Read more.
The synthesis and structural characterisation of phosphine-substituted alkynylboronates is reported. A P(III)-centred alkynylboronate (2) was prepared that showed little evidence for the conjugation of the P-lone pair to the boron via the alkyne π-system, as judged by X-ray crystallography studies of 2 and a related P(V) compound, 3. In addition, corresponding alkynyltrifluoroborate salts were prepared that showed improved stability by comparison to their boronic ester counterparts. These salts undergo Pd-catalysed cross-coupling reactions with aryl halides. Full article
(This article belongs to the Special Issue Recent Advances in Boron Chemistry)
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Review

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1191 KiB  
Review
Recent Developments in the Suzuki-Miyaura Reaction: 2010–2014
by Irene Maluenda and Oscar Navarro
Molecules 2015, 20(5), 7528-7557; https://doi.org/10.3390/molecules20057528 - 24 Apr 2015
Cited by 296 | Viewed by 18486
Abstract
The Suzuki-Miyaura reaction (SMR), involving the coupling of an organoboron reagent and an organic halide or pseudo-halide in the presence of a palladium or nickel catalyst and a base, has arguably become one of most utilized tools for the construction of a C-C [...] Read more.
The Suzuki-Miyaura reaction (SMR), involving the coupling of an organoboron reagent and an organic halide or pseudo-halide in the presence of a palladium or nickel catalyst and a base, has arguably become one of most utilized tools for the construction of a C-C bond. This review intends to be general account of all types of catalytic systems, new coupling partners and applications, including the literature between September 2010 and December 2014. Full article
(This article belongs to the Special Issue Recent Advances in Boron Chemistry)
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