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Organophosphorus Chemistry 2021
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Organophosphorus Chemistry 2021

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

Deadline for manuscript submissions: closed (15 July 2022) | Viewed by 27928

Special Issue Editor

Prof. Dr. György Keglevich

E-Mail Website
Guest Editor
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1521 Budapest, Hungary
Interests: organophosphorus chemistry; green chemistry; microwave chemistry; catalysts; ionic liquids
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

These days, organophosphorus (OP) chemistry forms an indispensable part of synthetic organic chemistry. OP compounds may be used as starting materials, intermediates, reagents, catalysts (phase transfer catalysts, organocatalysts, and ligands in P(III)-transition metal complexes) and solvents (ionic liquids (ILs)) in research laboratories and in the industry. There are a lot of frequently applied reactions, such as reductions, the Wittig reaction and its variations, especially the catalytic versions, the Arbuzov reaction, the Pudovik reaction, the Mitsunobu reaction, the Kabachnik-Fields reaction, etc. that apply P-containing reagents. The simple deoxygenation of phosphine oxides is also a challenging field. Other reactions, e.g., homogeneous catalytic transformations or C–C coupling reactions, involve P-ligands in catalysts. There has been an enormous development in the field of chiral OP compounds. Methods have been elaborated for the resolution of tertiary phosphine oxides and for enantioselective OP transformations. The optically active P(III) species may be used as ligands in transition metal (Pt, Pd, etc.) complex catalysts making stereoselective transformations possible. The heterocyclic discipline may include P-heterocycles and classical O- and N-heterocycles with P-functions. A special field comprises P-containing or P-functionalized macrocycles and other macromolecules, such as dendrimers. An up-to-date approach is to perform syntheses in the OP discipline in an environmentally friendly manner. This may include the use of microwave or ultrasound. Solvent-free accomplishments are also interesting. The use of IL-s including P-containing species as solvents or as additives is an up-to-date option. Monitoring reactions to optimize conditions or to observe reactive species is a challenging field. Theoretical calculations within OP chemistry are also an important field; these days, the evaluation of stereostructures and mechanisms may provide additional value information. A very important segment of OP chemistry, a driving force for development in fact, is the pool of biologically active OP compounds (e.g., bisphosphonic derivatives and aminophosphonic species) that are searched and used as drugs, or plant-protecting agents. Natural (e.g., peptide and amino acid) analogue P-compounds should also be mentioned. Lots of new phosphine oxides, phosphinates, phosphonates, and phosphoric esters have been described that may obtain different kinds of applications.

This special issue of Molecules will welcome all submissions that fit the above outline.

Prof. Dr. György Keglevich
Guest Editor

Manuscript Submission Information

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Keywords

  • organophosphorus chemistry
  • Arbuzov reaction
  • Pudovik reaction
  • Kabachnik–Fields reaction
  • Wittig reaction
  • deoxygenation
  • Mitsunobu reaction
  • Hirao reaction
  • phosphine chalcogenides
  • phosphines
  • phosphinic acids
  • phosphonic acids
  • phosphine boranes
  • phosphine complexes
  • P-heterocycles
  • macrocycles
  • dendrimers
  • catalysts
  • homogeneous catalysis
  • ionic liquids
  • microwave
  • ultrasound
  • monitoration
  • theoretical calculations
  • biologically active substrates
  • P-containing drugs
  • aminophosphonates
  • hydroxyphosphonates
  • dronic acid derivatives

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Published Papers (8 papers)

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Editorial

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3 pages, 187 KiB  
Editorial
Organophosphorus Chemistry 2021
by György Keglevich
Molecules 2023, 28(1), 394; https://doi.org/10.3390/molecules28010394 - 3 Jan 2023
Cited by 1 | Viewed by 1316
Abstract
Forty years have passed since a real “phosphabenzene” (a phosphinine) was prepared for the first time applying steric protection methodology with the sterically demanding 2,4,6-tri-tertiary-butylphenyl (“supermesityl”) group [...] Full article
(This article belongs to the Special Issue Organophosphorus Chemistry 2021)

Research

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14 pages, 2721 KiB  
Article
Practical Synthesis of Phosphinic Dipeptides by Tandem Esterification of Aminophosphinic and Acrylic Acids under Silylating Conditions
by Paraskevi Kokkala, Kostas Voreakos, Angelos Lelis, Konstantinos Patiniotis, Nikolaos Skoulikas, Laurent Devel, Angeliki Ziotopoulou, Eleni Kaloumenou and Dimitris Georgiadis
Molecules 2022, 27(4), 1242; https://doi.org/10.3390/molecules27041242 - 12 Feb 2022
Cited by 3 | Viewed by 2707
Abstract
In this report, a synthetic protocol for the preparation of phosphinic dipeptides of type 5 is presented. These compounds serve as valuable building blocks for the development of highly potent phosphinopeptidic inhibitors of medicinally relevant Zn-metalloproteases and aspartyl proteases. The proposed method is [...] Read more.
In this report, a synthetic protocol for the preparation of phosphinic dipeptides of type 5 is presented. These compounds serve as valuable building blocks for the development of highly potent phosphinopeptidic inhibitors of medicinally relevant Zn-metalloproteases and aspartyl proteases. The proposed method is based on the tandem esterification of α-aminophosphinic and acrylic acids under silylating conditions in order to subsequently participate in a P-Michael reaction. The scope of the transformation was investigated by using a diverse set of readily available acrylic acids and (R)-α-aminophosphinic acids, and high yields were achieved in all cases. In most examples reported herein, the isolation of biologically relevant (R,S)-diastereoisomers became possible by simple crystallization from the crude products, thus enhancing the operational simplicity of the proposed method. Finally, functional groups corresponding to acidic or basic natural amino acids are also compatible with the reaction conditions. Based on the above, we expect that the practicality of the proposed protocol will facilitate the discovery of pharmacologically useful bioactive phosphinic peptides. Full article
(This article belongs to the Special Issue Organophosphorus Chemistry 2021)
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Graphical abstract

11 pages, 5750 KiB  
Article
A Mechanistic Study on the Formation of Dronic Acids
by Péter Ábrányi-Balogh, István Greiner and György Keglevich
Molecules 2021, 26(24), 7587; https://doi.org/10.3390/molecules26247587 - 14 Dec 2021
Cited by 2 | Viewed by 2415
Abstract
Dronic acid derivatives, important drugs against bone diseases, may be synthesized from the corresponding substituted acetic acid either by reaction with phosphorus trichloride in methanesulfonic acid as the solvent or by using also phosphorous acid as the P-reactant if sulfolane is applied as [...] Read more.
Dronic acid derivatives, important drugs against bone diseases, may be synthesized from the corresponding substituted acetic acid either by reaction with phosphorus trichloride in methanesulfonic acid as the solvent or by using also phosphorous acid as the P-reactant if sulfolane is applied as the medium. The energetics of the two protocols were evaluated by high-level quantum chemical calculations on the formation of fenidronic acid and benzidronic acid. The second option, involving (HO)2P-O-PCl2 as the nucleophile, was found to be more favorable over the first variation, comprising Cl2P-O-SO2Me as the real reagent, especially for the case of benzidronate. Full article
(This article belongs to the Special Issue Organophosphorus Chemistry 2021)
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10 pages, 2401 KiB  
Article
Tetraalkyl Hydroxymethylene-bisphosphonate and Dialkyl 1-Diphenylphosphinoyl-1-hydroxy-ethylphosphonate Derivatives by the Pudovik Reaction and Their Rearranged Products
by Zsuzsanna Szalai and György Keglevich
Molecules 2021, 26(24), 7575; https://doi.org/10.3390/molecules26247575 - 14 Dec 2021
Cited by 5 | Viewed by 2159
Abstract
The reaction of diethyl α-oxoethylphosphonate and diethyl oxobenzylphosphonate with diethyl phosphite, dimethyl phosphite, and diphenylphosphine oxide affords, depending on the substrates and conditions (nature and quantity of the amine catalyst, temperature, and solvent), the Pudovik adduct and/or the corresponding >P(O)–CH–O–P(O)< product formed by [...] Read more.
The reaction of diethyl α-oxoethylphosphonate and diethyl oxobenzylphosphonate with diethyl phosphite, dimethyl phosphite, and diphenylphosphine oxide affords, depending on the substrates and conditions (nature and quantity of the amine catalyst, temperature, and solvent), the Pudovik adduct and/or the corresponding >P(O)–CH–O–P(O)< product formed by rearrangement. The nature of the substituent on the central carbon atom (a methyl or phenyl group) influences the inclination for the rearrangement. The asymmetric products (either adducts or rearranged species) with different P(O)Y functions (Y = RO or Ph) exhibit interesting NMR features. Full article
(This article belongs to the Special Issue Organophosphorus Chemistry 2021)
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14 pages, 5603 KiB  
Article
A Fast and Convenient Synthesis of New Water-Soluble, Polyanionic Dendrimers
by Grzegorz M. Salamończyk
Molecules 2021, 26(16), 4754; https://doi.org/10.3390/molecules26164754 - 6 Aug 2021
Cited by 4 | Viewed by 3869
Abstract
Reasonably simple, efficient, and possessing aspects of generality, the methodology for the synthesis of new, water-soluble, dendrimeric polyesters with great potential applications as antiviral drugs in their own right is described. The essential aspect of the presented approach is a quite unique, immediate [...] Read more.
Reasonably simple, efficient, and possessing aspects of generality, the methodology for the synthesis of new, water-soluble, dendrimeric polyesters with great potential applications as antiviral drugs in their own right is described. The essential aspect of the presented approach is a quite unique, immediate access to the polyanionic material at each generation during divergent synthesis. Six target polyanionic dendrimers (generations 1, 2, and 3) have been synthesized. The key monomers applied in this project were 1,3,5-benzenetricarboxylic acid derivatives, which also worked as direct precursors of the charged dendrimer surface. Full article
(This article belongs to the Special Issue Organophosphorus Chemistry 2021)
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Review

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21 pages, 20626 KiB  
Review
Chemistry of Several Sterically Bulky Molecules with P=P, P=C, and C≡P Bond
by Masaaki Yoshifuji
Molecules 2022, 27(5), 1557; https://doi.org/10.3390/molecules27051557 - 25 Feb 2022
Cited by 10 | Viewed by 2368
Abstract
Several sterically protected, low-coordinate organophosphorus compounds with P=P, P=C, and C≡P bond are described in this study. Molecules such as diphosphenes, phosphaalkenes, 1-phosphaallenes, 1,3-diphosphaallenes, 3,4-diphosphinidenecyclobutenes, and phosphaalkynes are stabilized with an extremely bulky 2,4,6-tri-t-butylphenyl (Mes*) group. The synthesis, structures, physical, and [...] Read more.
Several sterically protected, low-coordinate organophosphorus compounds with P=P, P=C, and C≡P bond are described in this study. Molecules such as diphosphenes, phosphaalkenes, 1-phosphaallenes, 1,3-diphosphaallenes, 3,4-diphosphinidenecyclobutenes, and phosphaalkynes are stabilized with an extremely bulky 2,4,6-tri-t-butylphenyl (Mes*) group. The synthesis, structures, physical, and chemical properties of these molecules are discussed, together with some successful applications in catalytic organic reactions. Full article
(This article belongs to the Special Issue Organophosphorus Chemistry 2021)
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28 pages, 8157 KiB  
Review
The Synthesis of Hypodiphosphoric Acid and Derivatives with P-P Bond, including Esters and Diphosphine Dioxides: A Review
by Jacek E. Nycz
Molecules 2021, 26(23), 7286; https://doi.org/10.3390/molecules26237286 - 30 Nov 2021
Cited by 4 | Viewed by 2440
Abstract
The synthesis of hypodiphosphoric acid and its related compounds began in 1877, but no summary of the synthetic efforts has been reported. This review includes published papers related to the molecules containing the >P(=O)-P(=O)< fragment, which notably resembles the structure of the >P(=O)-O-P(=O)< [...] Read more.
The synthesis of hypodiphosphoric acid and its related compounds began in 1877, but no summary of the synthetic efforts has been reported. This review includes published papers related to the molecules containing the >P(=O)-P(=O)< fragment, which notably resembles the structure of the >P(=O)-O-P(=O)< moiety, the essential building block of many important molecules found in nature and in the field of medicinal chemistry. This review covers the strategies related to the synthesis of hypodiphosphoric acid (former name hypophosphoric acid), its ester form, and diphosphine dioxides. Finally, some properties and applications of these structures studied during this period are presented. Full article
(This article belongs to the Special Issue Organophosphorus Chemistry 2021)
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33 pages, 13286 KiB  
Review
The Hydrolysis of Phosphinates and Phosphonates: A Review
by Nikoletta Harsági and György Keglevich
Molecules 2021, 26(10), 2840; https://doi.org/10.3390/molecules26102840 - 11 May 2021
Cited by 20 | Viewed by 9239
Abstract
Phosphinic and phosphonic acids are useful intermediates and biologically active compounds which may be prepared from their esters, phosphinates and phosphonates, respectively, by hydrolysis or dealkylation. The hydrolysis may take place both under acidic and basic conditions, but the C-O bond may also [...] Read more.
Phosphinic and phosphonic acids are useful intermediates and biologically active compounds which may be prepared from their esters, phosphinates and phosphonates, respectively, by hydrolysis or dealkylation. The hydrolysis may take place both under acidic and basic conditions, but the C-O bond may also be cleaved by trimethylsilyl halides. The hydrolysis of P-esters is a challenging task because, in most cases, the optimized reaction conditions have not yet been explored. Despite the importance of the hydrolysis of P-esters, this field has not yet been fully surveyed. In order to fill this gap, examples of acidic and alkaline hydrolysis, as well as the dealkylation of phosphinates and phosphonates, are summarized in this review. Full article
(This article belongs to the Special Issue Organophosphorus Chemistry 2021)
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