Green chemical syntheses and applications within organophosphorus chemistry

Keglevich, György; Grűn, Alajos; Bálint, Erika; Kiss, Nóra Zsuzsa; Bagi, Péter; Tőke, Lásʐló

doi:10.1007/s11224-016-0847-1

Cited by 9 publications

(4 citation statements)

References 90 publications

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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%

“…In the last decade, there has been an increased focus on development of new synthetic methodologies for P-C bond formation. As a result, new novel and green methodologies [ 24 , 28 ] in the organic synthesis gave impetus to replace toxic and harmful phosphorus starting materials with more benign alternatives [ 31 ].…”

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%

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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: General Principles Of P-c Bond Formationmentioning

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 have aroused the continuing strong interest of synthetic chemists over the past few decades due to their great importance and wide applications in medicinal chemistry, organic synthesis, ligand chemistry, and materials science . Among them, γ-ketophosphonates and γ-ketophosphine oxides have received considerable attention because of their unusual structural features and their association with wide-ranging biological activities and unique properties .…”

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confidence: 99%

Zn(OTf)₂-Catalyzed Phosphinylation of Propargylic Alcohols: Access to γ-Ketophosphine Oxides

et al. 2017

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The first facile and efficient Zn(OTf)-catalyzed direct coupling of unprotected propargylic alcohols with arylphosphine oxides has been developed, affording a general, one-step approach to access structurally diverse γ-ketophosphine oxides via sequential Meyer-Schuster rearrangement/phospha-Michael reaction along with new C(sp)-P and C═O bond formations, operational simplicity, and complete atom economy under ligand-free and base-free conditions.

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Catalyst‐ and Additive‐Free Decarboxylative C‐4 Phosphorylation of Coumarin‐3‐Carboxylic Acids at Ambient Conditions

Brahmachari

2020

Adv Synth Catal

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Green chemical syntheses and applications within organophosphorus chemistry

Cited by 9 publications

References 90 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

Zn(OTf)₂-Catalyzed Phosphinylation of Propargylic Alcohols: Access to γ-Ketophosphine Oxides

Catalyst‐ and Additive‐Free Decarboxylative C‐4 Phosphorylation of Coumarin‐3‐Carboxylic Acids at Ambient Conditions

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Green chemical syntheses and applications within organophosphorus chemistry

Cited by 9 publications

References 90 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

Zn(OTf)2-Catalyzed Phosphinylation of Propargylic Alcohols: Access to γ-Ketophosphine Oxides

Catalyst‐ and Additive‐Free Decarboxylative C‐4 Phosphorylation of Coumarin‐3‐Carboxylic Acids at Ambient Conditions

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Zn(OTf)₂-Catalyzed Phosphinylation of Propargylic Alcohols: Access to γ-Ketophosphine Oxides