Sulfuric acid-modified PEG-6000 (PEG-OSO3H): an efficient Brönsted acid–surfactant combined catalyst for the one-pot three component synthesis of α-aminonitriles in water

Shekouhy, Mohsen

doi:10.1039/c2cy00493c

Cited by 48 publications

(9 citation statements)

References 60 publications

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“…A comparison study between the current method using Fe 3 O 4 @SiO 2 -APTES-TFA and the previously reported results [31][32][33][34][35][36][37][38] is summarized in Table 4. The results show that this method has a comparable result in terms of yield and reaction time, and fast recycling of the catalyst from the reaction medium (using a magnetic field) without the need for tedious and energy-consuming filtration and centrifugation, which can be seen in the reported catalytic systems in the Table S1.…”

Section: Resultsmentioning

confidence: 98%

Synthesis of α‐Aminonitriles and 5‐Substituted 1H‐Tetrazoles Using an Efficient Nanocatalyst of Fe₃O₄@SiO₂–APTES‐supported Trifluoroacetic Acid

Fatahi

Jafarzadeh

Pourmanouchehri

2019

Journal of Heterocyclic Chem

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Fe3O4@SiO2–APTES‐supported trifluoroacetic acid nanocatalyst was used for the one‐pot synthesis of α‐aminonitriles via a three‐component reaction of aldehydes (or ketones), amines, and sodium cyanide. This method produced a high yield of 75–96% using only a small amount of the catalyst (0.05 g) in EtOH at room temperature. The catalyst was also employed for the synthesis of 5‐substituted 1H‐tetrazoles from nitriles and sodium azide in EtOH at 80°C. The tetrazoles were produced with good‐to‐excellent yields in a short reaction time of 4 h. Both synthetic methods were carried out in the absence of an organic volatile solvent. Because the supported trifluoroacetic acid generated a solid acid on the surface, thus the acid corrosiveness was not a serious challenge. This heterogeneous nanocatalyst was magnetically recovered and reused several times without significant loss of catalytic activity.

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Section: Resultsmentioning

confidence: 98%

Synthesis of α‐Aminonitriles and 5‐Substituted 1H‐Tetrazoles Using an Efficient Nanocatalyst of Fe₃O₄@SiO₂–APTES‐supported Trifluoroacetic Acid

Fatahi

Jafarzadeh

Pourmanouchehri

2019

Journal of Heterocyclic Chem

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“…The same year, Yang et al investigated the synthesis of 3-hydroxy-5,5-dimethyl-2-[phenyl(phenylthio)methyl]cyclohex-2-enone with aromatic aldehydes, substituted thiophenols, and 5,5-dimethyl-1,3-cyclohexanedione under similar experimental conditions [93]. These reactions were carried out in 20-92% yields at 25 • C within 1-6 h. Numerous catalytic systems based on surfactants are now used to boost multicomponent reactions (e.g., Biginelli [94], Kabachnik-Fields [95], Strecker [96], and Hantzsch [97]). For more information on this topic and for other multicomponent reactions, we advise that the reader refer to the recent review of Ostaszewski and coworkers [98].…”

Section: Micelles and Emulsionsmentioning

confidence: 99%

Supramolecular Chemistry and Self-Organization: A Veritable Playground for Catalysis

2019

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The directed assembly of molecular building blocks into discrete supermolecules or extended supramolecular networks through noncovalent intermolecular interactions is an ongoing challenge in chemistry. This challenge may be overcome by establishing a hierarchy of intermolecular interactions that, in turn, may facilitate the edification of supramolecular assemblies. As noncovalent interactions can be used to accelerate the reaction rates and/or to increase their selectivity, the development of efficient and practical catalytic systems, using supramolecular chemistry, has been achieved during the last few decades. However, between discrete and extended supramolecular assemblies, the newly developed “colloidal tectonics” concept allows us to link the molecular and macroscopic scales through the structured engineering of colloidal structures that can be applied to the design of predictable, versatile, and switchable catalytic systems. The main cutting-edge strategies involving supramolecular chemistry and self-organization in catalysis will be discussed and compared in this review.

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“…The reaction described by Strecker between a carbonyl compound, amine and cyanide anion is one of the most powerful tools for the synthesis of α-aminonitriles, which can be further hydrolyzed to the corresponding α-amino acids (Scheme 7 ; Shafran et al, 1989 ). Among variety of catalytic systems for the Strecker reaction, Shekouhy ( 2012 ) reported the application of sulfuric acid-modified polyethylene glycol (PEG-OSO 3 H) as a Bronsted acid–surfactant combined catalyst (micellar catalysis type 2), which enabled to perform this reaction in water. The author has optimized the reaction conditions including solvent type, temperature and different catalytic systems based on sulfuric or Lewis acids.…”

Section: The Strecker Reactionmentioning

confidence: 99%

Multicomponent Reactions Accelerated by Aqueous Micelles

et al. 2018

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Multicomponent reactions are powerful synthetic tools for the efficient creation of complex organic molecules in an one-pot one-step fashion. Moreover, the amount of solvents and energy needed for separation and purification of intermediates is significantly reduced what is beneficial from the green chemistry issues point of view. This review highlights the development of multicomponent reactions conducted using aqueous micelles systems during the last two decades.

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Sulfuric acid-modified PEG-6000 (PEG-OSO3H): an efficient Brönsted acid–surfactant combined catalyst for the one-pot three component synthesis of α-aminonitriles in water

Cited by 48 publications

References 60 publications

Synthesis of α‐Aminonitriles and 5‐Substituted 1H‐Tetrazoles Using an Efficient Nanocatalyst of Fe₃O₄@SiO₂–APTES‐supported Trifluoroacetic Acid

Synthesis of α‐Aminonitriles and 5‐Substituted 1H‐Tetrazoles Using an Efficient Nanocatalyst of Fe₃O₄@SiO₂–APTES‐supported Trifluoroacetic Acid

Supramolecular Chemistry and Self-Organization: A Veritable Playground for Catalysis

Multicomponent Reactions Accelerated by Aqueous Micelles

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Sulfuric acid-modified PEG-6000 (PEG-OSO3H): an efficient Brönsted acid–surfactant combined catalyst for the one-pot three component synthesis of α-aminonitriles in water

Cited by 48 publications

References 60 publications

Synthesis of α‐Aminonitriles and 5‐Substituted 1H‐Tetrazoles Using an Efficient Nanocatalyst of Fe3O4@SiO2–APTES‐supported Trifluoroacetic Acid

Synthesis of α‐Aminonitriles and 5‐Substituted 1H‐Tetrazoles Using an Efficient Nanocatalyst of Fe3O4@SiO2–APTES‐supported Trifluoroacetic Acid

Supramolecular Chemistry and Self-Organization: A Veritable Playground for Catalysis

Multicomponent Reactions Accelerated by Aqueous Micelles

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Product

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Synthesis of α‐Aminonitriles and 5‐Substituted 1H‐Tetrazoles Using an Efficient Nanocatalyst of Fe₃O₄@SiO₂–APTES‐supported Trifluoroacetic Acid

Synthesis of α‐Aminonitriles and 5‐Substituted 1H‐Tetrazoles Using an Efficient Nanocatalyst of Fe₃O₄@SiO₂–APTES‐supported Trifluoroacetic Acid