Silver‐Mediated Phosphonylation of C(sp<sup>2</sup>)−H Bonds with P−H Bonds: Direct C−H Functionalization of Ferrocenyl Anilides and Dialkyl Phosphites under Palladium‐ and Copper‐Free Conditions

Yu, Xinyan; Ge, Bingyang; Zhang, Yaxuan; Wang, Xiaoli; Wang, Dawei

doi:10.1002/ajoc.201600296

Cited by 13 publications

(5 citation statements)

References 108 publications

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“…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%

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%

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

et al. 2017

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“…In 2015, Yuan et al [102] developed the silver-catalyzed direct C(sp 2 )-H radical phosphorylation of coumarins with H-phosphites, affording selective coumarin-3-yl phosphonate in moderate to good yields. In 2016, a silver-mediated C-H phosphonylation reaction of ferrocenyl anilides with dialkyl phosphites was developed [Figure 67] [103] . The method is free of palladium and copper catalysts and tolerates a variety of functional groups.…”

Section: Dehydrogenative C-h Phosphorylationmentioning

confidence: 99%

Advances in radical phosphorylation from 2016 to 2021

Liu¹,

Xiao²,

Fu³

et al. 2021

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Organophosphorus compounds are of great significance in organic chemistry. Therefore, the construction of phosphorus-containing compounds has attracted significant attention from organic chemists. Radical phosphorylation has become a powerful strategy for building organophosphorus compounds and numerous achievements have been realized in recent years. In this review, we summarize the development of the generation and application of phosphorus radicals in organic chemistry since 2016. Special emphasis is given to various new transformations involving the generation of P-centered radicals via transition metal catalytic, photochemical and electrochemical means. Recent advances in the development of metal-free catalytic phosphorylations involving Pcentered radicals are also reviewed.

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“…[11] Lanthanide elements are the treasure house of multifunctional materials with excellent magnetic, optical, and electrical properties. [12][13][14][15] However, new non-centrosymmetric (NCS) lanthanide compounds are hard to obtain because the high coordinated lanthanide polyhedrons are preferred to form CS infinite frameworks. As the retrieved result from the Inorganic Crystal Structure Database, the proportion of NCS compounds in lanthanide oxides is ≈12.4%, which is far lower than that in all inorganic compounds (≈18%).…”

Section: Introductionmentioning

confidence: 99%

Ln₂F₂(OH₂)(MoO₃)₂(SeO₃)₂: Promising Multifunctional Nonlinear Optical Materials Created by Partial Fluorination Strategy under Corrosion Resistant Supercritical Reactions

Ma,

Li,

et al. 2023

Advanced Science

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It has historically been exceedingly challenging to create physically and chemically stable lanthanide compounds with strong second harmonic generation (SHG) due to their strong preference to central symmetry. In this work, five new non‐centrosymmetric lanthanide selenites, namely, Ln2F2(OH2)(MoO3)2(SeO3)2 (Ln = Sm, Eu, Gd, Tb and Dy), are achieved by partial fluorination of the lanthanide oxygen polyhedron. An HF corrosion resistant supercritical hydrothermal method is developed, which is a facile and universal method for HF corrosion and high‐temperature high‐pressure environment. The title compounds displayed a novel 3D framework composed of 1D molybdenum selenite chains bridged by Ln2F2O12(OH2) dimers. Their powder SHG responses showed a large difference, ranging from 1.0 to 9.0 × KH2PO4 (KDP) at 1064 nm. The half‐filled Gd compound exhibited very strong SHG efficiency of up to 1.2 × KTP (KTiOPO4) at 2050 nm. Compounds Tb and Gd are the first lanthanide selenites with SHG intensity reaching KTP level, which is very rare in this system. Furthermore, these compounds can also possess excellent physicochemical stability and strong luminescence emission, indicating that they are promising multifunctional nonlinear optical materials. This work offered an effective way for design and synthesis of multifunctional and high‐performant nonlinear optical materials.

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Silver‐Mediated Phosphonylation of C(sp²)−H Bonds with P−H Bonds: Direct C−H Functionalization of Ferrocenyl Anilides and Dialkyl Phosphites under Palladium‐ and Copper‐Free Conditions

Cited by 13 publications

References 108 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

Advances in radical phosphorylation from 2016 to 2021

Ln₂F₂(OH₂)(MoO₃)₂(SeO₃)₂: Promising Multifunctional Nonlinear Optical Materials Created by Partial Fluorination Strategy under Corrosion Resistant Supercritical Reactions

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Silver‐Mediated Phosphonylation of C(sp2)−H Bonds with P−H Bonds: Direct C−H Functionalization of Ferrocenyl Anilides and Dialkyl Phosphites under Palladium‐ and Copper‐Free Conditions

Cited by 13 publications

References 108 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

Advances in radical phosphorylation from 2016 to 2021

Ln2F2(OH2)(MoO3)2(SeO3)2: Promising Multifunctional Nonlinear Optical Materials Created by Partial Fluorination Strategy under Corrosion Resistant Supercritical Reactions

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Silver‐Mediated Phosphonylation of C(sp²)−H Bonds with P−H Bonds: Direct C−H Functionalization of Ferrocenyl Anilides and Dialkyl Phosphites under Palladium‐ and Copper‐Free Conditions

Ln₂F₂(OH₂)(MoO₃)₂(SeO₃)₂: Promising Multifunctional Nonlinear Optical Materials Created by Partial Fluorination Strategy under Corrosion Resistant Supercritical Reactions