Recent Advances in H-Phosphonate Chemistry. Part 2. Synthesis of C-Phosphonate Derivatives

Sobkowski, Michał; Kraszewski, Adam; Stawiński, Jacek

doi:10.1007/128_2014_563

Cited by 6 publications

(5 citation statements)

References 208 publications

(242 reference statements)

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“…The P-C bond formation has been reviewed in the past by various researchers [ 6 , 8 , 9 , 10 , 12 , 13 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 ]. Conventional synthetic strategies like Michael addition, Arbuzov rearrangement reactions, Friedel–Crafts reactions, radical addition reactions, Pudovik reactions are the most common strategy for P-C bond creation.…”

Section: General Principles Of P-c Bond Formationmentioning

confidence: 99%

“…Accordingly, the chemical reactivity of the organophosphorus compounds can be influenced by their structural geometry and valency of the phosphorus atom. For example, H -phosphonates with P(O)H bonds are commonly used as starting materials for P-C bond formation and thus their chemical reactions have been investigated in detail [ 6 , 9 , 12 , 24 , 25 , 29 , 30 , 31 , 33 , 34 ]. It is reported that presence of the P=O bond is the driving force for their reactions [ 23 ].…”

Section: General Principles Of P-c Bond Formationmentioning

confidence: 99%

“…P-C containing organophosphorus compounds find application as metal complex catalysts [ 1 ], reagents in organic chemistry [ 2 , 3 ], pesticides, insecticides, herbicides, medicine and biological systems [ 4 ], additives for polymers [ 5 ], surfactants, lubricants [ 6 ], surface treatments on metals [ 7 ], etc. In the past few decades, many review articles and book chapters regarding the creation of P-C bond and their potential applications have been published [ 6 , 8 , 9 , 10 , 11 , 12 , 13 ]. Organophosphorus compounds with P-C bonds are increasingly investigated as flame retardants due their high thermal and hydrolytic stability (P-C bond), ease of synthesis and suitability of processing at high temperature.…”

Section: Introductionmentioning

confidence: 99%

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Recent Developments in Organophosphorus Flame Retardants Containing P-C Bond and Their Applications

et al. 2017

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Organophosphorus compounds containing P-C bonds are increasingly developed as flame retardant additives due to their excellent thermal and hydrolytic stability and ease of synthesis. The latest development (since 2010) in organophosphorus flame retardants containing P-C bonds summarized in this review. In this review, we have broadly classified such phosphorus compounds based on the carbon unit linked to the phosphorus atom i.e., could be a part of either an aliphatic or an aromatic unit. We have only considered those published literature where a P-C bond was created as a part of synthetic strategy to make either an intermediate or a final organophosphorus compound with an aim to use it as a flame retardant. General synthetic strategies to create P-C bonds are briefly discussed. Most popular synthetic strategies used for developing P-C containing phosphorus based flame retardants include Michael addition, Michaelis–Arbuzov, Friedels–Crafts and Grignard reactions. In general, most flame retardant derivatives discussed in this review have been prepared via a one- to two-step synthetic strategy with relatively high yields greater than 80%. Specific examples of P-C containing flame retardants synthesized via suitable synthetic strategy and their applications on various polymer systems are described in detail. Aliphatic phosphorus compounds being liquids or low melting solids are generally applied in polymers via coatings (cellulose) or are incorporated in the bulk of the polymers (epoxy, polyurethanes) during their polymerization as reactive or non-reactive additives. Substituents on the P atoms and the chemistry of the polymer matrix greatly influence the flame retardant behavior of these compounds (condensed phase vs. the gas phase). Recently, aromatic DOPO based phosphinate flame retardants have been developed with relatively higher thermal stabilities (>250 °C). Such compounds have potential as flame retardants for high temperature processable polymers such as polyesters and polyamides. A vast variety of P-C bond containing efficient flame retardants are being developed; however, further work in terms of their economical synthetic methods, detailed impact on mechanical properties and processability, long term durability and their toxicity and environmental impact is much needed for their potential commercial exploitations.

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Section: General Principles Of P-c Bond Formationmentioning

confidence: 99%

Section: General Principles Of P-c Bond Formationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Recent Developments in Organophosphorus Flame Retardants Containing P-C Bond and Their Applications

et al. 2017

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“…They find their use as insecticides, plant growth regulators, − herbicides, pesticides, fungicides, and in photosynthesis as ADP and ATP. In the industry, they are used as additive polymers, surfactants, lubricants, surface treaters on metals, and flame retardants . In organic chemistry, they have been used as catalysts in coupling and complex reactions and also as catalytic promoters .…”

Section: Introductionmentioning

confidence: 99%

Green Synthesis, Antioxidant, and Plant Growth Regulatory Activities of Novel α-Furfuryl-2-alkylaminophosphonates

et al. 2021

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A series of novel α-furfuryl-2-alkylaminophosphonates have been efficiently synthesized from the one-pot threecomponent classical Kabachnik−Fields reaction in a green chemical approach by addition of an in situ generated dialkylphosphite to Schiff's base of aldehydes and amines by using environmental and eco-friendly silica gel supported iodine as a catalyst by microwave irradiation. The advantage of this protocol is simplicity in experimental procedures and products were resulted in high isolated yields. The synthesized α-furfuryl-2alkylaminophosphonates were screened to in vitro antioxidant and plant growth regulatory activities and some are found to be potent with antioxidant and plant growth regulatory activities. These in vitro studies have been further supported by ADMET (absorption, distribution, metabolism, excretion, and toxicity), quantitative structure−activity relationship, molecular docking, and bioactivity studies and identified that they were potentially bound to the GLN340 amino acid residue in chain C of 1DNU protein and TYR597 amino acid residue in chain A of 4M7E protein, causing potential exhibition of antioxidant and plant growth regulatory activities. Eventually, title compounds are identified as good blood− brain barrier (BBB)-penetrable compounds and are considered as proficient central nervous system active and neuroprotective antioxidant agents as the neuroprotective property is determined with BBB penetration thresholds.

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“…Phosphorous acid (H 3 PO 3 ) and its conjugate base, phosphite (HPO 3 2– ), have found applications as reducing agents, as cathode materials for lithium- and sodium-ion batteries, − as well as the starting material for other commercially important reduced phosphorus compounds, such as glyphosate . Phosphite and related H -phosphonate esters are a family of key intermediates to organophosphorus compounds via elaboration of the P–H function into P–C bonds. − Recent advances in biotechnology have also cleared out a path for phosphite to act as an environmentally friendly herbicide, biostimulant, and biocide in modern agriculture owing to its minimal toxicity to humans and animals, biodegradability in soil, and inability to trigger eutrophication of natural water bodies through agricultural runoff . The development of transgenic crops that metabolize phosphite rather than phosphate has allowed phosphite to serve as both a fertilizer and herbicide. , Additionally, phosphite is thought to have been a potential major nutrient in the preoxygenated Archaen oceans, and the oxidation and condensation reactivity of inorganic phosphite likely mediated prebiotic formation of condensed phosphates. − …”

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confidence: 99%

Sustainable Production of Reduced Phosphorus Compounds: Mechanochemical Hydride Phosphorylation Using Condensed Phosphates as a Route to Phosphite

et al. 2022

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In pursuit of a more sustainable production of phosphorous acid (H 3 PO 3 ), a versatile chemical with phosphorus in the +3 oxidation state, we herein report that condensed phosphates can be employed to phosphorylate hydride reagents under solvent-free mechanochemical conditions to furnish phosphite (HPO 3 2– ). Using potassium hydride as the hydride source, sodium trimetaphosphate (Na 3 P 3 O 9 ), triphosphate (Na 5 P 3 O 10 ), pyrophosphate (Na 4 P 2 O 7 ), fluorophosphate (Na 2 PO 3 F), and polyphosphate (“(NaPO 3 ) n ”) engendered phosphite in optimized yields of 44, 58, 44, 84, and 55% based on total P content, respectively. Formation of overreduced products including hypophosphite (H 2 PO 2 – ) was identified as a competing process, and mechanistic investigations revealed that hydride attack on in-situ-generated phosphorylated phosphite species is a potent pathway for overreduction. The phosphite generated from our method was easily isolated in the form of barium phosphite, a useful intermediate for production of phosphorous acid. This method circumvents the need to pass through white phosphorus (P 4 ) as a high-energy intermediate and mitigates involvement of environmentally hazardous chemicals. A bioproduced polyphosphate was found to be a viable starting material for the production of phosphite. These results demonstrate the possibility of accessing reduced phosphorus compounds in a more sustainable manner and, more importantly, a means to close the modern phosphorus cycle.

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Recent Advances in H-Phosphonate Chemistry. Part 2. Synthesis of C-Phosphonate Derivatives

Cited by 6 publications

References 208 publications

Recent Developments in Organophosphorus Flame Retardants Containing P-C Bond and Their Applications

Recent Developments in Organophosphorus Flame Retardants Containing P-C Bond and Their Applications

Green Synthesis, Antioxidant, and Plant Growth Regulatory Activities of Novel α-Furfuryl-2-alkylaminophosphonates

Sustainable Production of Reduced Phosphorus Compounds: Mechanochemical Hydride Phosphorylation Using Condensed Phosphates as a Route to Phosphite

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