Recent progress toward organophosphorus compounds based on phosphorus-centered radical difunctionalizations

Gao, Yuzhen; Tang, Guo; Zhao, Yufen

doi:10.1080/10426507.2017.1295965

Cited by 86 publications

(44 citation statements)

References 49 publications

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“…Organophosphorus compounds are well-known for their medicinal, biological, or specific material-related properties and have found wide applications in pharmaceutical chemistry, biochem- istry, and materials science [21][22][23][24][25][26]. They represent also excellent ligands for many metals and have been used in catalytic systems for a huge number of organic reactions [21][22][23][24][25][26]. Due to the importance of the chroman-4-one scaffold on one hand and that of organophosphorus compounds on the other, the development of concise and efficient approaches for the synthesis of chroman-4-one derivatives decorated with phosphorus functionalities [27,28], thus combining the characteristics of both components in one molecule may find useful applications.…”

Section: Introductionmentioning

confidence: 99%

Metal-free synthesis of phosphinoylchroman-4-ones via a radical phosphinoylation–cyclization cascade mediated by K₂S₂O₈

Liu¹,

Lu²,

Xie³

et al. 2020

Beilstein J. Org. Chem.

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A variety of chroman-4-ones bearing phosphine oxide motifs were conveniently synthesized from readily available diphenylphosphine oxides and alkenyl aldehydes via a metal-free tandem phosphinoylation/cyclization protocol. The reaction utilizes K2S2O8 as oxidant and proceeds in DMSO/H2O at environmentally benign conditions with a broad substrate scope and afforded the title compounds in moderate yields.

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Section: Introductionmentioning

confidence: 99%

Metal-free synthesis of phosphinoylchroman-4-ones via a radical phosphinoylation–cyclization cascade mediated by K₂S₂O₈

Liu¹,

Lu²,

Xie³

et al. 2020

Beilstein J. Org. Chem.

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“…Since phosphorus-containing motives are present in a variety of medicinally pertinent synthetic targets, ligand of metal complex catalysts, materials, and so on, development of selective, sustainable, and efficient technologies to construct these kinds of organic structures is of crucial importance [1,2,3,4,5,6,7]. Organophosphorus compounds with P–C bonds containing a phosphonate group P(O)(OAlk) 2 or phosphonic acid R–PO(OH) 2 residues are an important class of substrates because they have broad applications in various areas of human livelihood [8,9,10,11,12].…”

Section: Introductionmentioning

confidence: 99%

“…The importance of direct C–H aromatic phosphorylation reactions from the point of view of both “green” chemistry and the search for new, more efficient ways of obtaining practically important organophosphorus compounds led to a sharp increase in the number of studies in this area. However, as it turned out, product yields were highly dependent on the reaction conditions, and the optimal oxidizing agents and catalysts were chosen empirically in each case, which was laborious and required screening for each specific substrate [6,13,14,15]. Reaction mechanisms were studied in detail only in rare cases and, as a rule, were postulated.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of Transition Metal Catalysts in Electrochemically Induced Aromatic Phosphonation

2019

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Voltammetry provides important information on the redox properties of catalysts (transition metal complexes of Ni, Co, Mn, etc.) and their activity in electrocatalytic reactions of aromatic C–H phosphonation in the presence of a phosphorus precursor, for example, dialkyl-H-phosphonate. Based on catalytic current growth of oxidation or reduction of the metal catalysts (CoII, MnII, NiII, MnII/NiII, MnII/CoII, and CoII/NiII), quantitative characteristics of the regeneration of catalysts were determined, for example, for MnII, NiII and MnII/NiII, CoII/NiII pairs. Calculations confirmed the previously made synthetic observations on the synergistic effect of certain metal ions in binary catalytic systems (MnIIbpy/NiIIbpy and NiIIbpy/CoIIbpy); for mixtures, the observed rate constants, or TOF, were 690 s−1 and 721 s−1, respectively, and product yields were higher for monometallic catalytic systems (up to 71% for bimetallic catalytic systems and ~30% for monometallic catalytic systems). In some cases, the appearance of pre-waves after adding H-phosphonates confirmed the preceding chemical reaction. It also confirmed the formation of metal phosphonates in the time scale of voltammetry, oxidizing or reducing at lower potentials than the original (RO)2P(O)H and metal complex, which could be used for fast diagnostics of metal ion and dialkyl-H-phosphonate interactions. Electrochemical transfer of an electron to (from) metal phosphonate generates a phosphonyl radical, which can then react with different arenes to give the products of aromatic C–H phosphonation.

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“…Over the past century, the use of organophosphorus compounds has been extensively explored due to their versatility [1,2]. This exploration has paved the way to develop new synthetic methodologies and further the design of new organophosphorus compounds [3,4].…”

Section: Introductionmentioning

confidence: 99%

One-Pot Synthesis of P(O)-N Containing Compounds Using N-Chlorosuccinimide and Their Influence in Thermal Decomposition of PU Foams

et al. 2018

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Synthesis of intermediate containing P( O )-Cl bonds is the key to converting P( O )-H bonds to P( O )-N. In this work we have performed chlorination reactions of different H -phosphinates and H -phosphonates using N -chlorosuccinimide as an environmentally-benign chlorinating agent. The chlorination reaction showed high yield and high selectivity for transformation of P( O )-H bonds into P( O )-Cl analogues, resulting in an easily separable succinimide as the by-product. Using a one-pot synthesis methodology, we have synthesized a series of P( O )-N containing derivatives whose synthesis was found to be dependent on the reaction solvents and the starting materials. The synthesized P( O )-N compounds were incorporated in flexible polyurethane foam (FPUF) and screened for their influence in thermal decomposition of FPUFs using thermogravimetric analysis (TGA) and a microscale combustion calorimeter (MCC). All solid P( O )-N compounds influenced the first-stage decomposition of FPUFs, which resulted in an accelerated decomposition or temporary stabilization of this stage. However, the liquid P( O )-N derivatives volatilize at an earlier stage and could be active in the gas phase. In addition, they also work in condensed phase via acid catalyzed decomposition for FPUFs.

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Recent progress toward organophosphorus compounds based on phosphorus-centered radical difunctionalizations

Cited by 86 publications

References 49 publications

Metal-free synthesis of phosphinoylchroman-4-ones via a radical phosphinoylation–cyclization cascade mediated by K₂S₂O₈

Metal-free synthesis of phosphinoylchroman-4-ones via a radical phosphinoylation–cyclization cascade mediated by K₂S₂O₈

Evaluation of Transition Metal Catalysts in Electrochemically Induced Aromatic Phosphonation

One-Pot Synthesis of P(O)-N Containing Compounds Using N-Chlorosuccinimide and Their Influence in Thermal Decomposition of PU Foams

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Recent progress toward organophosphorus compounds based on phosphorus-centered radical difunctionalizations

Cited by 86 publications

References 49 publications

Metal-free synthesis of phosphinoylchroman-4-ones via a radical phosphinoylation–cyclization cascade mediated by K2S2O8

Metal-free synthesis of phosphinoylchroman-4-ones via a radical phosphinoylation–cyclization cascade mediated by K2S2O8

Evaluation of Transition Metal Catalysts in Electrochemically Induced Aromatic Phosphonation

One-Pot Synthesis of P(O)-N Containing Compounds Using N-Chlorosuccinimide and Their Influence in Thermal Decomposition of PU Foams

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Metal-free synthesis of phosphinoylchroman-4-ones via a radical phosphinoylation–cyclization cascade mediated by K₂S₂O₈

Metal-free synthesis of phosphinoylchroman-4-ones via a radical phosphinoylation–cyclization cascade mediated by K₂S₂O₈