Synthesis of phosphonates in a continuous flow manner

Tóth, Nóra; Tajti, Ádám; Ladányi-Pára, Katalin; Bálint, Erika; Keglevich, György

doi:10.1080/10426507.2018.1528253

Cited by 3 publications

(4 citation statements)

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“…[38] Using a combined microwave-flow system as well, Bálint, Keglevich and colleagues reported the continuous flow transesterification of dimethyl-and diethyl H-phosphonate using different linear aliphatic alcohols. [39,40] Depending on the reaction parameters, the fate of the reaction could be tuned and could promote either the mono-or the disubstitution towards the corresponding H-phosphonate 21 or 22, respectively. Aliphatic alcohol 20 was used in a 25-fold excess and premixed with the H-phosphonate 19 prior to the injection in the MW chamber.…”

Section: Eurjocmentioning

confidence: 99%

“…Continuous flow transesterification of dimethyl-and diethyl H-phosphonate through a microwave-assisted procedure. [39,40]…”

Section: Eurjocmentioning

confidence: 99%

“…Following a preliminary report, [40] Bálint, Keglevich and coworkers studied the catalyst-free synthesis of various α-aryl-αaminophosphonates under microwave-assisted continuous flow conditions according to a three-component Kabachnik-Fields reaction. [73] Optimization of the system was performed using a model reaction involving aniline, benzaldehyde and diethyl phosphite in a batch MW reactor.…”

Section: Aza-pudovik and Kabachnik-fields Reactionsmentioning

confidence: 99%

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Continuous Flow Organophosphorus Chemistry

2020

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Organophosphorus derivatives are widespread compounds that chemists find from the bench to the plant, with numerous daily life applications. Besides their common utility for a wide range of notorious reactions such as the Wittig and Horner‐Wadsworth‐Emmons olefinations, the Arbuzov reaction, the Staudinger reaction, the Mitsunobu reaction as well as ligands for a large variety of organometallic complexes, organophosphorus compounds have also found numerous applications as active pharmaceutical ingredients and agrochemicals. Some organophosphorus derivatives are also infamously known as Chemical Warfare Agents. Within the context of generalized adoption of new process technologies in the Chemistry Toolbox, this review intends to give an update on the most recent and significant advances in continuous flow organophosphorus chemistry. Selected examples in methodology, total synthesis and for the preparation of industrially relevant targets are discussed for illustrating the assets of flow chemistry.

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Section: Eurjocmentioning

confidence: 99%

“…Continuous flow transesterification of dimethyl-and diethyl H-phosphonate through a microwave-assisted procedure. [39,40]…”

Section: Eurjocmentioning

confidence: 99%

Section: Aza-pudovik and Kabachnik-fields Reactionsmentioning

confidence: 99%

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Continuous Flow Organophosphorus Chemistry

2020

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“…Novel reaction conditions based on activation by alternative energy inputs in "batch" (microwaves, 21,33 ultrasounds 34 ) or under continuous flow, [35][36] with sustainable solvents 37 or solvent-free 24 (including manual grinding in a mortar), 38 catalyzed or not, were explored to improve the selectivity, the reaction efficiency, and the environmental footprint of KF-3CR compared to the conventional methods in solution. 17,24,26 To our surprise, no reports deal with the use of mechanochemical procedures for the preparation of α-aminophosphonic acid derivatives and more generally for the formation of C(sp 3 )-phosphorus bonds, while only one account describes the metal-catalyzed C(sp 2 )phosphorus bond formation in a ball-mill.…”

Section: Introductionmentioning

confidence: 99%

Kabachnik–Fields Reaction by Mechanochemistry: New Horizons from Old Methods

Fiore

Sović

Lukin

et al. 2020

ACS Sustainable Chem. Eng.

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-Aminophosphonates are an important class of biologically active compounds, attracting considerable attention in medicinal chemistry, by inhibiting enzymes involved in amino acid metabolism. Herein, the Kabachnik-Fields domino reaction was investigated by mechanochemistry for the first-time preparation of -aminophosphonate derivatives in high yields and with full selectivity, outperforming comparable solution procedures. The reaction is a Lewis acid-catalysed process occurring however without the addition of any external catalyst, but occurring on the surface of the zirconium oxide used as the milling media. The mechanism of the mechanochemical reaction was also investigated by in situ Raman spectroscopy, the kinetic behavior was disclosed. The solid-state structures of two representative compounds have been determined by single-crystal X-ray diffractions.

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Integration of molecular and computational approaches paints a holistic portrait of obscure metabolisms

Reyes-Umana,

Ewens,

Meier

et al. 2023

mBio

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Microorganisms are essential drivers of earth’s geochemical cycles. However, the significance of elemental redox cycling mediated by microorganisms is often underestimated beyond the most well-studied nutrient cycles. Phosphite, (per)chlorate, and iodate are each considered esoteric substrates metabolized by microorganisms. However, recent investigations have indicated that these metabolisms are widespread and ubiquitous, affirming a need to continue studying the underlying microbiology to understand their biogeochemical effects and their interface with each other and our biosphere. This review focuses on combining canonical techniques of culturing microorganisms with modern omic approaches to further our understanding of obscure metabolic pathways and elucidate their importance in global biogeochemical cycles. Using these approaches, marker genes of interest have already been identified for phosphite, (per)chlorate, and iodate using traditional microbial physiology and genetics. Subsequently, their presence was queried to reveal the distribution of metabolic pathways in the environment using publicly available databases. In conjunction with each other, computational and experimental techniques provide a more comprehensive understanding of the location of these microorganisms, their underlying biochemistry and genetics, and how they tie into our planet’s geochemical cycles.

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Synthesis of phosphonates in a continuous flow manner

Cited by 3 publications

References 4 publications

Continuous Flow Organophosphorus Chemistry

Continuous Flow Organophosphorus Chemistry

Kabachnik–Fields Reaction by Mechanochemistry: New Horizons from Old Methods

Integration of molecular and computational approaches paints a holistic portrait of obscure metabolisms

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