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Modern Organophosphorus Chemistry
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Modern Organophosphorus Chemistry

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

Deadline for manuscript submissions: closed (28 February 2023) | Viewed by 12802

Special Issue Editors

Dr. Viktor Iaroshenko

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Guest Editor
Division of Wood Chemistry and Pulp Technology, Department of Fiber and Polymer Technology, School of Chemistry, Biotechnology and Health, KTH Royal Institute of Technology, Teknikringen 56-58, SE-100 44 Stockholm, Sweden
Interests: mechanochemistry, catalysis; photoredox catalysis; functionalization of C-H bond; C-C and C-Het couplings; medicinal chemistry; heterocycles; element-organic chemistry; fluorine; phosphorus; green chemistry; sustainability
Special Issues, Collections and Topics in MDPI journals
Dr. Satenik Satenik Mkrtchyan

E-Mail Website
Guest Editor
Department of Chemistry, Faculty of Natural Sciences, Matej Bel University, Tajovkého 40, 97401 Banska Bystrica, Slovakia
Interests: C-C and C-Het couplings; phosphorus chemistry; catalysis; heterocycles; fluorine; mechanochemistry; green chemistry; sustainability
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Organophosphorus compounds play an important role in nature, as well as in different natural sciences, such as medicine chemistry, agriculture, material science and catalytic science. In recent decades, a number of drugs and drug candidates from purine/pyrimidine antimetabolite series, among others, furnished with phosphate or related phosphorus-containing functional groups, have appeared on the market or have been developed and successfully entered into clinical studies. Simultaneously, we are facing the advent of new phosphorus-containing advanced organic materials and new phosphine ligands that may change our understanding of homogenous and heterogeneous catalysis. The intensive development of the field demands new literature to deliver novel views, concepts and trends. This Special Issue aims to showcase the recent advances in the different aspects of organophosphorus chemistry and related disciplines, where organophosphorus compounds have found an intensive application, with the main emphasis on the synthesis, properties and application of phosphorus-containing complex organic molecules. Our goal is to provide the broad readerships of this journal with the latest updates in the field, which will cover numerous aspects of contemporary organophosphorus chemistry.

We are pleased to invite experts in the field to publish their latest developments and concepts in this Special Issue in the form of short communications, full-length papers, perspectives and reviews. We hope that this acquired knowledge will provide further insight and a solid pool of data for future developments in organophosphorus chemistry and its related fields.

Dr. Viktor O. Iaroshenko
Dr. Satenik Satenik Mkrtchyan
Guest Editors

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

  • organophosphorus chemistry
  • reactivity and structure of organophosphorus compounds
  • phosphorus-containing heterocycles
  • ionic liquids
  • homogenous and heterogenies catalysis
  • phosphorus in all aspects of catalysis, green chemistry and sustainability
  • phosphorus in polymers and organic materials
  • phosphorus in supramolecular chemistry
  • phosphorus in biologically active compounds, medicinal chemistry, drug discovery, life sciences, biology and crop science
  • spectroscopic techniques in organophosphorus chemistry
  • phosphorus compounds in the environment

Published Papers (5 papers)

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Research

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10 pages, 3125 KiB  
Article
Microwave-Accelerated McKenna Synthesis of Phosphonic Acids: An Investigation
by Dana Mustafa, Justin M. Overhulse, Boris A. Kashemirov and Charles E. McKenna
Molecules 2023, 28(8), 3497; https://doi.org/10.3390/molecules28083497 - 15 Apr 2023
Cited by 1 | Viewed by 1651
Abstract
Phosphonic acids represent one of the most important categories of organophosphorus compounds, with myriad examples found in chemical biology, medicine, materials, and other domains. Phosphonic acids are rapidly and conveniently prepared from their simple dialkyl esters by silyldealkylation with bromotrimethylsilane (BTMS), followed by [...] Read more.
Phosphonic acids represent one of the most important categories of organophosphorus compounds, with myriad examples found in chemical biology, medicine, materials, and other domains. Phosphonic acids are rapidly and conveniently prepared from their simple dialkyl esters by silyldealkylation with bromotrimethylsilane (BTMS), followed by desilylation upon contact with water or methanol. Introduced originally by McKenna, the BTMS route to phosphonic acids has long been a favored method due to its convenience, high yields, very mild conditions, and chemoselectivity. We systematically investigated microwave irradiation as a means to accelerate the BTMS silyldealkylations (MW-BTMS) of a series of dialkyl methylphosphonates with respect to solvent polarity (ACN, dioxane, neat BTMS, DMF, and sulfolane), alkyl group (Me, Et, and iPr), electron-withdrawing P-substitution, and phosphonate–carboxylate triester chemoselectivity. Control reactions were performed using conventional heating. We also applied MW-BTMS to the preparation of three acyclic nucleoside phosphonates (ANPs, an important class of antiviral and anticancer drugs), which were reported to undergo partial nucleoside degradation under MW hydrolysis with HCl at 130–140 °C (MW-HCl, a proposed alternative to BTMS). In all cases, MW-BTMS dramatically accelerated quantitative silyldealkylation compared to BTMS with conventional heating and was highly chemoselective, confirming it to be an important enhancement of the conventional BTMS method with significant advantages over the MW-HCl method. Full article
(This article belongs to the Special Issue Modern Organophosphorus Chemistry)
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11 pages, 1131 KiB  
Communication
Ortho-Phosphinoarenesulfonamide-Mediated Staudinger Reduction of Aryl and Alkyl Azides
by Xingzhuo Li, Zhenguo Wang, Wenjun Luo, Zixu Wang, Keshu Yin and Le Li
Molecules 2022, 27(17), 5707; https://doi.org/10.3390/molecules27175707 - 5 Sep 2022
Cited by 3 | Viewed by 2181
Abstract
Conventional Staudinger reductions of organic azides are sluggish with aryl or bulky aliphatic azides. In addition, Staudinger reduction usually requires a large excess of water to promote the decomposition of the aza-ylide intermediate into phosphine oxide and amine products. To overcome the [...] Read more.
Conventional Staudinger reductions of organic azides are sluggish with aryl or bulky aliphatic azides. In addition, Staudinger reduction usually requires a large excess of water to promote the decomposition of the aza-ylide intermediate into phosphine oxide and amine products. To overcome the challenges above, we designed a novel triaryl phosphine reagent 2c with an ortho-SO2NH2 substituent. Herein, we report that such phosphine reagents are able to mediate the Staudinger reduction of both aryl and alkyl azides in either anhydrous or wet solvents. Good to excellent yields were obtained in all cases (even at a diluted concentration of 0.01 M). The formation of B-TAP, a cyclic aza-ylide, instead of phosphine oxide, eliminates the requirement of water in the Staudinger reduction. In addition, computational studies disclose that the intramolecular protonation of the aza-ylide by the ortho-SO2NH2 group is kinetically favorable and responsible for the acceleration of Staudinger reduction of the aryl azides. Full article
(This article belongs to the Special Issue Modern Organophosphorus Chemistry)
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15 pages, 12257 KiB  
Article
Photoinduced Bisphosphination of Alkynes with Phosphorus Interelement Compounds and Its Application to Double-Bond Isomerization
by Yuki Yamamoto, Ryo Tanaka, Shintaro Kodama, Akihiro Nomoto and Akiya Ogawa
Molecules 2022, 27(4), 1284; https://doi.org/10.3390/molecules27041284 - 14 Feb 2022
Cited by 7 | Viewed by 2061
Abstract
The addition of interelement compounds with heteroatom-heteroatom single bonds to carbon-carbon unsaturated bonds under light irradiation is believed to be an atomically efficient method to procure materials with carbon-heteroatom bonds. In this study, we achieved the photoinduced bisphosphination of alkynes using the phosphorus [...] Read more.
The addition of interelement compounds with heteroatom-heteroatom single bonds to carbon-carbon unsaturated bonds under light irradiation is believed to be an atomically efficient method to procure materials with carbon-heteroatom bonds. In this study, we achieved the photoinduced bisphosphination of alkynes using the phosphorus interelement compound, tetraphenyldiphosphine monosulfide (1), to stereoselectively obtain the corresponding (E)-vic-1,2-bisphosphinoalkenes, which are important transition-metal ligands. The bisphosphination reaction was performed by mixing 1 and various alkynes and then exposing the mixture to light irradiation. Optimization of the conditions for the bisphosphination reaction resulted in a wide substrate range and excellent trans-selectivity. Moreover, the completely regioselective introduction of pentavalent and trivalent phosphorus groups to the terminal and internal positions of the alkynes, respectively, was achieved. We also found that the novel double-bond isomerization reaction of the synthesized bisphosphinated products occurred with a catalytic amount of a base under mild conditions. Our method for the photoinduced bisphosphination of carbon-carbon unsaturated compounds may have strong implications for both organic synthesis and organometallic and catalyst chemistry. Full article
(This article belongs to the Special Issue Modern Organophosphorus Chemistry)
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27 pages, 15365 KiB  
Article
Synthesis and Antiproliferative Activity of Phosphorus Substituted 4-Cyanooxazolines, 2-Aminocyanooxazolines, 2-Iminocyanooxazolidines and 2-Aminocyanothiazolines by Rearrangement of Cyanoaziridines
by Victor Carramiñana, Ana M. Ochoa de Retana, Francisco Palacios and Jesús M. de los Santos
Molecules 2021, 26(14), 4265; https://doi.org/10.3390/molecules26144265 - 14 Jul 2021
Cited by 5 | Viewed by 2192
Abstract
Several phosphorus-substituted N-acylated cyanoaziridines 2 and N-carbamoylated cyanoziridines 5 were prepared in good to high yields. N-Acylated cyanoaziridines 2 were used, after ring expansion, in an efficient synthesis of oxazoline derivative 3a and in a completely regio-controlled reaction in the [...] Read more.
Several phosphorus-substituted N-acylated cyanoaziridines 2 and N-carbamoylated cyanoziridines 5 were prepared in good to high yields. N-Acylated cyanoaziridines 2 were used, after ring expansion, in an efficient synthesis of oxazoline derivative 3a and in a completely regio-controlled reaction in the presence of NaI. Conversely, N-carbamoyl cyanoaziridines 5 reacted with NaI to obtain a regioisomeric mixture of 2-aminocyanooxazolines 7. Mild acidic conditions can be used for the isomerization of N-thiocarbamoyl cyanoaziridine 6a into a 2-aminocyanothiazoline derivative 8a by using BF3·OEt2 as a Lewis acid. Likewise, a one pot reaction of NH-cyanoaziridines 1 with isocyanates obtained 2-iminocyanooxazolidines 9 regioselectively. This synthetic methodology involves the addition of isocyanates to starting cyanoaziridines to obtain N-carbamoyl cyanoaziridines 5, which after the ring opening, reacts with a second equivalent of isocyanate to give the final 2-imino cyanooxazolidines 9. In addition, the cytotoxic effect on the cell lines derived from human lung adenocarcinoma (A549) was also screened. 2-Iminooxazolidines 9 exhibited moderate activity against the A549 cell line in vitro. Furthermore, a selectivity towards cancer cells (A549) over non-malignant cells (MCR-5) was detected. Full article
(This article belongs to the Special Issue Modern Organophosphorus Chemistry)
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Review

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20 pages, 42965 KiB  
Review
Nickel Complexes in C‒P Bond Formation
by Almaz A. Zagidullin, Il’yas F. Sakhapov, Vasili A. Miluykov and Dmitry G. Yakhvarov
Molecules 2021, 26(17), 5283; https://doi.org/10.3390/molecules26175283 - 31 Aug 2021
Cited by 11 | Viewed by 3393
Abstract
This review is a comprehensive account of reactions with the participation of nickel complexes that result in the formation of carbon–phosphorus (C‒P) bonds. The catalytic and non-catalytic reactions with the participation of nickel complexes as the catalysts and the reagents are described. The [...] Read more.
This review is a comprehensive account of reactions with the participation of nickel complexes that result in the formation of carbon–phosphorus (C‒P) bonds. The catalytic and non-catalytic reactions with the participation of nickel complexes as the catalysts and the reagents are described. The various classes of starting compounds and the products formed are discussed individually. The several putative mechanisms of the nickel catalysed reactions are also included, thereby providing insights into both the synthetic and the mechanistic aspects of this phosphorus chemistry. Full article
(This article belongs to the Special Issue Modern Organophosphorus Chemistry)
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