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Recent Progress in Organophosphorus Chemistry
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Recent Progress in Organophosphorus Chemistry

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

Deadline for manuscript submissions: 31 July 2024 | Viewed by 5515

Special Issue Editors

Prof. Dr. Jean-Luc Montchamp

E-Mail Website
Guest Editor
Department of Chemistry and Biochemistry, Texas Christian University, TCU Box 298860, Fort Worth, TX 76129, USA
Interests: organophosphorus; methodology; synthesis; catalysis; heterocycles; asymmetric
Dr. Karen R. Winters

E-Mail Website
Guest Editor Assistant
Vertex Pharmaceuticals, 3215 Merryfield Row, San Diego, CA 92121, USA
Interests: organic chemistry; medicinal chemistry; biochemistry

Special Issue Information

Dear Colleagues,

Phosphorus is undeniably a key element in the periodic table. Phosphorus is a necessary component of all known forms of life and many important biomolecules, such as nucleic acids, phospholipids, glucose-6-phosphate, and ATP, to name only a few. As a result, its largest industrial use is in fertilizers, such as those made from inorganic phosphorus. However, organophosphorus compounds also have many important applications in flame retardants, extractants, corrosion inhibitors, pesticides, medicines, ligands for metal-catalyzed reactions, and even organocatalysts. The particularly impressive practicality of phosphorus is causing renewed research activity.

This Special Issue entitled "Recent Progress in Organophosphorus Chemistry" aims to present all aspects of the current original research, from synthetic methodology to catalysis, and from materials to biologically active compounds. Review articles on the most advanced research topics are also considered.

Prof. Dr. Jean-Luc Montchamp
Guest Editor

Dr. Karen R. Winters
Guest Editor Assistant

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

  • phosphorus
  • catalysis
  • methodology
  • synthesis
  • materials
  • bioactivity
  • ligand
  • asymmetric
  • chirality

Published Papers (5 papers)

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Research

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16 pages, 3448 KiB  
Article
Synthesis of Aminobisphosphinates through a Cascade Reaction between Hypophosphorous Acid and Bis(trimethylsilyl)imidates Mediated by ZnI2
by Nouha Ayadi, Aurélie Descamps, Thibaut Legigan, Jade Dussart-Gautheret, Maelle Monteil, Evelyne Migianu-Griffoni, Taïcir Ben Ayed, Julia Deschamp and Marc Lecouvey
Molecules 2023, 28(17), 6226; https://doi.org/10.3390/molecules28176226 - 24 Aug 2023
Viewed by 788
Abstract
Among phosphorylated derivatives, phosphinates occupy a prominent place due to their ability to be bioisosteres of phosphates and carboxylates. These properties imply the necessity to develop efficient methodologies leading to phosphinate scaffolds. In recent years, our team has explored the nucleophilic potential of [...] Read more.
Among phosphorylated derivatives, phosphinates occupy a prominent place due to their ability to be bioisosteres of phosphates and carboxylates. These properties imply the necessity to develop efficient methodologies leading to phosphinate scaffolds. In recent years, our team has explored the nucleophilic potential of silylated phosphonite towards various electrophiles. In this paper, we propose to extend our study to other electrophiles. We describe here the implementation of a cascade reaction between (trimethylsilyl)imidates and hypophosphorous acid mediated by a Lewis acid allowing the synthesis of aminomethylenebisphosphinate derivatives. The present study focuses on methodological development including a careful NMR monitoring of the cascade reaction. The optimized conditions were successfully applied to various aliphatic and aromatic substituted (trimethylsilyl)imidates, leading to the corresponding AMBPi in moderate to good yields. Full article
(This article belongs to the Special Issue Recent Progress in Organophosphorus Chemistry)
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14 pages, 2689 KiB  
Article
Enhanced LC-ESI-MS/MS Sensitivity by Cationic Derivatization of Organophosphorus Acids
by Tamar Shamai Yamin, Moran Madmon, Ariel Hindi, Avital Shifrovich, Hagit Prihed, Merav Blanca and Avi Weissberg
Molecules 2023, 28(16), 6090; https://doi.org/10.3390/molecules28166090 - 16 Aug 2023
Viewed by 1052
Abstract
The chemical derivatization to enhance the signal intensity and signal-to-noise (S/N) of several organophosphorus (OP) acids in liquid chromatography tandem mass spectrometry (LC-ESI-MS/MS) is illustrated. The OP class of compounds represents the environmental degradants of OP nerve agents and pesticides. N-(2-(bromomethyl)benzyl)-N,N-diethylethanaminium bromide (CAX-B) [...] Read more.
The chemical derivatization to enhance the signal intensity and signal-to-noise (S/N) of several organophosphorus (OP) acids in liquid chromatography tandem mass spectrometry (LC-ESI-MS/MS) is illustrated. The OP class of compounds represents the environmental degradants of OP nerve agents and pesticides. N-(2-(bromomethyl)benzyl)-N,N-diethylethanaminium bromide (CAX-B) was utilized to derivatize a panel of eight acids consisting of five alkyl methylphosphonic acids (ethyl-, isopropyl-, isobutyl-, cyclohexyl-, and pinacolyl-methylphosphonic acid) along with three dialkylphosphate analogs (diethyl-, dibutyl-, and diethyl thio-phosphate). The derivatization reaction with CAX-B was conducted in acetonitrile in the presence of potassium carbonate at 70 °C for 1 h. The resulting acid derivatives were analyzed with an LC-Orbitrap-ESI-MS/MS, and their dissociation processes were investigated. It was found that the derivatization procedure increased the limits of identification (LOIs) by one to over two orders of magnitude from the range of 1 to 10 ng/mL for the intact OP-acids to the range of 0.02–0.2 ng/mL for the derivatized acids utilizing an LC-MS(QqQ) in MRM mode, regardless of the sample matrix (hair, concrete, or plant extracts). The interpretation of the corresponding ESI-MS/MS spectra for each type of derivatized sub-OP family revealed the formation of characteristic neutral losses and a characteristic ion for the organophosphorus core. This derivatization is beneficial and useful for screening and identifying target and “unknown” OP acids. Full article
(This article belongs to the Special Issue Recent Progress in Organophosphorus Chemistry)
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12 pages, 1028 KiB  
Article
Synthesis and Characterization of a New Series of Bis(allylic-α-aminophosphonates) under Mild Reaction Conditions
by Ichrak Souii, Med Abderrahmane Sanhoury, Javier Vicario, Xabier Jiménez-Aberásturi, Mohamed L. Efrit, Hedi M’rabet and Jesús M. de los Santos
Molecules 2023, 28(12), 4678; https://doi.org/10.3390/molecules28124678 - 09 Jun 2023
Viewed by 1208
Abstract
Several bis(α-aminophosphonates) have been conveniently prepared in good yields using a straightforward multicomponent Kabachnik–Fields reaction between ethane 1,2-diamine or propane 1,3-diamine, diethylphosphite and aldehydes under catalyst-free conditions. The nucleophilic substitution reaction of bis(α-aminophosphonates) prepared and ethyl (2-bromomethyl)acrylate under mild reaction conditions afforded an [...] Read more.
Several bis(α-aminophosphonates) have been conveniently prepared in good yields using a straightforward multicomponent Kabachnik–Fields reaction between ethane 1,2-diamine or propane 1,3-diamine, diethylphosphite and aldehydes under catalyst-free conditions. The nucleophilic substitution reaction of bis(α-aminophosphonates) prepared and ethyl (2-bromomethyl)acrylate under mild reaction conditions afforded an original synthetic approach to a new series of bis(allylic-α-aminophosphonates). Full article
(This article belongs to the Special Issue Recent Progress in Organophosphorus Chemistry)
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11 pages, 4756 KiB  
Article
New Optically Active tert-Butylarylthiophosphinic Acids and Their Selenium Analogues as the Potential Synthons of Supramolecular Organometallic Complexes: Syntheses and Crystallographic Structure Determination
by Jarosław Błaszczyk, Bogdan Bujnicki, Patrycja Pokora-Sobczak, Grażyna Mielniczak, Lesław Sieroń, Piotr Kiełbasiński and Józef Drabowicz
Molecules 2023, 28(11), 4298; https://doi.org/10.3390/molecules28114298 - 24 May 2023
Viewed by 934
Abstract
The aim of the research described in this publication is two-fold. The first is a detailed description of the synthesis of a series of compounds containing a stereogenic heteroatom, namely the optically active P-stereogenic derivatives of tert-butylarylphoshinic acids bearing sulfur or [...] Read more.
The aim of the research described in this publication is two-fold. The first is a detailed description of the synthesis of a series of compounds containing a stereogenic heteroatom, namely the optically active P-stereogenic derivatives of tert-butylarylphoshinic acids bearing sulfur or selenium. The second is a detailed discussion dedicated to the determination of their structures by an X-ray analysis. Such a determination is needed when considering optically active hetero-oxophosphoric acids as new chiral solvating agents, precursors of new chiral ionic liquids, or ligands in complexes serving as novel organometallic catalysts. Full article
(This article belongs to the Special Issue Recent Progress in Organophosphorus Chemistry)
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Review

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18 pages, 7005 KiB  
Review
Strategies for the Preparation of Phosphorus Janus Dendrimers and Their Properties
by Joel Cejas-Sánchez, Anna Kajetanowicz, Karol Grela, Anne-Marie Caminade and Rosa María Sebastián
Molecules 2023, 28(14), 5570; https://doi.org/10.3390/molecules28145570 - 21 Jul 2023
Cited by 1 | Viewed by 957
Abstract
Dendrimers, being highly branched monodispersed macromolecules, predominantly exhibit identical terminal functionalities within their structural framework. Nonetheless, there are instances where the presence of two distinct surface functionalities becomes advantageous for the fulfilment of specific properties. To achieve this objective, one approach involves implementing [...] Read more.
Dendrimers, being highly branched monodispersed macromolecules, predominantly exhibit identical terminal functionalities within their structural framework. Nonetheless, there are instances where the presence of two distinct surface functionalities becomes advantageous for the fulfilment of specific properties. To achieve this objective, one approach involves implementing Janus dendrimers, consisting of two dendrimeric wedges terminated by dissimilar functionalities. The prevalent method for creating these structures involves the synthesis of dendrons that possess a core functionality that complements that of a second dendron, facilitating their coupling to generate the desired dendrimers. In this comprehensive review, various techniques employed in the fabrication of phosphorus-based Janus dendrimers are elucidated, displaying the different coupling methodologies employed between the two units. The advantages of phosphorus dendrimers over classic dendrimers will be shown, as the presence of at least one phosphorus atom in each generation allows for the easy monitoring of reactions and the confirmation of purity through a simple technique such as 31P NMR, as these structures typically exhibit easily interpretable patterns. Full article
(This article belongs to the Special Issue Recent Progress in Organophosphorus Chemistry)
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