The Phosphorus Aspects of Green Chemistry: the Use of Quaternary Phosphonium Salts and 1,3-Dialkylimidazolium Hexafluorophosphates in Organic Synthesis

Keglevich, György; Baan, Zoltan; Hermecz, István; Novák, Tibor; Odinets, Irina L.

doi:10.2174/138527207779316552

Cited by 48 publications

(16 citation statements)

References 122 publications

(149 reference statements)

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“…[13] The ionic liquids have also been entering organophosphorus chemistry. [14,15] Of the various reactions in organophosphorus chemistry, the MA reaction effectively progressed in less reaction time with good yields in numerous ILs such as [Rmim][X] (X = Br, BF 4 , PF 6 , NTf 2 ). [16] Recently, room-temperature ionic liquids (RTILs), especially 1,3-dialkylimidazolium salts as green solvents, offer several benefits in synthetic organic chemistry with respect to environmental perspectives [17,18] because of their high thermal stability, negligible vapor pressure, recyclability, and immiscibility with a number of organic solvents.…”

Section: Introductionmentioning

confidence: 99%

Expeditious, Nano-BF₃ · SiO₂-Catalyzed Michaelis–Arbuzov Reaction in an Ionic Liquid: Synthesis of Privileged Aryl/Heterocyclic Phosphonates

Rasheed

Rao

Subramanyam

et al. 2014

Synthetic Communications

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An expeditious, simple, and green method was developed for the synthesis of privileged aryl/heterocyclicphosphonates, 8(a-c) to 13(a-c) through Michaelis-Arbuzov reaction of aryl=heterocyclic halides (Br), 1-6, and trialkylphosphites, 7(a-c), in roomtemperature ionic liquid [bbim]Br using heterogeneous Lewis catalyst, nano-silica-supported boron trifluoride (BF 3 -SiO 2 ). The advantages of this protocol are simplicity, good yield of the products, less reaction time (20-38 min), mild reaction conditions, easy workup, and reusability of the catalyst and ionic liquid. It is demonstrated that nano-BF 3 -SiO 2 is a recoverable and easy accessible catalyst for the formation of C(sp 2 )-P bond in an ionic liquid.

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Section: Introductionmentioning

confidence: 99%

Expeditious, Nano-BF₃ · SiO₂-Catalyzed Michaelis–Arbuzov Reaction in an Ionic Liquid: Synthesis of Privileged Aryl/Heterocyclic Phosphonates

Rasheed

Rao

Subramanyam

et al. 2014

Synthetic Communications

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“…The prominent role of these compounds is to convert the carbonyl groups to carbon-carbon double bonds 7 . From the large number of methods available for the synthesis of phosphorus ylides, the most important one involves the reaction of a phosphonium salt with a base 14,20 . In recent years a method has been developed for the preparation of this family by using a novel approach employing vinyl phosphonium salts 15,16 .…”

Section: Introductionmentioning

confidence: 99%

Structural effects of different NH-acids and dialkyl acetylenedicarboxylates on the kinetic parameters of stable phosphorus ylids: a mechanistic investigation

Zakarianejad¹,

Habibi‐Khorassani²,

Makiabadi³

et al. 2013

10.5267/j.ccl

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Kinetic studies were made of the reactions between triphenylphosphine 1 and dialkyl acetylenedicarboxylates 2, in the presence of NH-acids, such as benzotriazole, 5-methylbenzotriazole or 5-chlorobenzotriazole 3 (as a protic/nucleophilic reagent). To determine the kinetic parameters of the reactions, they were monitored by UV spectrophotometry. Useful information was obtained from studies of the effect of solvent, structure of reactants (dialkyl acetylenedicarboxylates and NH-acids) and also concentration of reactants on the reaction rates. First and third steps (k 2 , k 3 ) of all reactions were recognized as a rate determining and fast steps, respectively. Proposed mechanism was confirmed on the basis of experimental data.

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“…compounds is to convert the carbonyl groups to carbon-carbon double bonds 7 from the large number of methods available for the synthesis of phosphorus ylides, the most important involve the reaction of a phosphonium salt with a base 14,20 . In recent years a method has been developed for the preparation of this family by using a novel approach employing vinyl phosphonium salts 15,16 .…”

Section: Introductionmentioning

confidence: 99%

Understanding the Mechanism of Stable Phosphorus Ylides Derived from Imidazole, 2-Methylimidazole or 4-Methylimidazole: A Kinetic Study

Zakarianezhad¹,

Habibi‐Khorassani²,

Maghsoodlou³

et al. 2012

Orientjchem.

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Kinetic studies have been made for synthesis of stable phosphorus ylids in the presence of different NH-acids, such as Imidazole, 2-Methylimidazole or 4-Methylimidazole (as a protic/ nucleophilic reagent). At different temperature range studied, the dependence of the second order rate constant (ln k 2 ) and (ln k 2 /T) on reciprocal temperature was in a good agreement with Arrhenius and Eyring equations. This provided the relevant plots to calculate the activation parameters (Ea, ΔH # , ΔS # and ΔG # ) of all reactions. Furthermore, useful information were obtained from studies of the effect of solvent, structure of reactants (dialkyl acetylenedicarboxylates) and also concentration of reactants on the reaction rates. Proposed mechanism was confirmed according to the obtained results and steady state approximation, first and third steps (k 2 and k 3 ) of all reactions was recognized as a rate determining and fast steps, respectively on the basis of experimental data.

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The Phosphorus Aspects of Green Chemistry: the Use of Quaternary Phosphonium Salts and 1,3-Dialkylimidazolium Hexafluorophosphates in Organic Synthesis

Cited by 48 publications

References 122 publications

Expeditious, Nano-BF₃ · SiO₂-Catalyzed Michaelis–Arbuzov Reaction in an Ionic Liquid: Synthesis of Privileged Aryl/Heterocyclic Phosphonates

Expeditious, Nano-BF₃ · SiO₂-Catalyzed Michaelis–Arbuzov Reaction in an Ionic Liquid: Synthesis of Privileged Aryl/Heterocyclic Phosphonates

Structural effects of different NH-acids and dialkyl acetylenedicarboxylates on the kinetic parameters of stable phosphorus ylids: a mechanistic investigation

Understanding the Mechanism of Stable Phosphorus Ylides Derived from Imidazole, 2-Methylimidazole or 4-Methylimidazole: A Kinetic Study

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The Phosphorus Aspects of Green Chemistry: the Use of Quaternary Phosphonium Salts and 1,3-Dialkylimidazolium Hexafluorophosphates in Organic Synthesis

Cited by 48 publications

References 122 publications

Expeditious, Nano-BF3 · SiO2-Catalyzed Michaelis–Arbuzov Reaction in an Ionic Liquid: Synthesis of Privileged Aryl/Heterocyclic Phosphonates

Expeditious, Nano-BF3 · SiO2-Catalyzed Michaelis–Arbuzov Reaction in an Ionic Liquid: Synthesis of Privileged Aryl/Heterocyclic Phosphonates

Structural effects of different NH-acids and dialkyl acetylenedicarboxylates on the kinetic parameters of stable phosphorus ylids: a mechanistic investigation

Understanding the Mechanism of Stable Phosphorus Ylides Derived from Imidazole, 2-Methylimidazole or 4-Methylimidazole: A Kinetic Study

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Expeditious, Nano-BF₃ · SiO₂-Catalyzed Michaelis–Arbuzov Reaction in an Ionic Liquid: Synthesis of Privileged Aryl/Heterocyclic Phosphonates

Expeditious, Nano-BF₃ · SiO₂-Catalyzed Michaelis–Arbuzov Reaction in an Ionic Liquid: Synthesis of Privileged Aryl/Heterocyclic Phosphonates