Silica Gel Supported Ferric Perchlorate: A New and Efficient Reagent for One Pot Synthesis of Amides from Benzylic Alcohols

Salehi, Peyman; Motlagh, A. R.

doi:10.1080/00397910008087369

Cited by 27 publications

(9 citation statements)

References 9 publications

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“…Different acidic reagents were used for the expedition of Ritter reaction [77][78][79][80][81], which many of them suffer from at least one of the following disadvantages: unavailability of the reagent, vigorous reaction conditions, high cost and toxicity of the reagent, tedious work-up procedure, low yields, and inefficiency in amidation of saturated alcohols. Different acidic reagents were used for the expedition of Ritter reaction [77][78][79][80][81], which many of them suffer from at least one of the following disadvantages: unavailability of the reagent, vigorous reaction conditions, high cost and toxicity of the reagent, tedious work-up procedure, low yields, and inefficiency in amidation of saturated alcohols.…”

Section: Formation and Cleavage Of Carbon-nitrogen Bondsmentioning

confidence: 99%

Applications of Some Metal Hydrogen Sulfates in Organic Transformations

Zolfigol¹,

Shirini²,

Salehi³

et al. 2008

COC

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Sodium, magnesium, ferric, zirconium and aluminum hydrogen sulfates have been used as efficient reagents in organic chemistry. A broad range of reactions including deprotection, oxidation, C-C, C-N and C-O bond formation and cleavage took place in the presence of these reagents under mild and completely heterogeneous reaction conditions in good to high yields. In many cases the reagents were recycled and reused. This article is dedicated to Professor Naser Iranpoor who dedicates himself to the progress of science of organic chemistry in Iran and also teaches us how to live and love.

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Section: Formation and Cleavage Of Carbon-nitrogen Bondsmentioning

confidence: 99%

Applications of Some Metal Hydrogen Sulfates in Organic Transformations

Zolfigol¹,

Shirini²,

Salehi³

et al. 2008

COC

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“…However, by applying Fe(ClO 4 ) 3 on silica gel a stable nonhygroscopic reagent is obtained that can be used without special precautions and attention [9].…”

Section: Ferric Perchloratementioning

confidence: 99%

“…The mixture was stirred for 30 min and the solvent evaporated under reduced pressure. The resulting brown powder was further dried in a vacuum drying cabinet at 60 o C and reduced pressure (20 mm Hg) [9].…”

Section: Preparation Of Ferric Perchlorate On Silica Gelmentioning

confidence: 99%

Hydrated ferric perchlorate, Fe(ClO4)3.XH2O in organic synthesis. A short review

Heravi

Behbahani

2007

JICS

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“…Furthermore, this method is harmful to the environment due to untreated toxic alkyl halides and undesired waste. [11] In recent years, ferric perchlorate immobilized on silica gel as a heterogeneous catalyst has been used in organic syntheses. [8][9][10] Ferric perchlorate is a transition metal Lewis acid that acts as an inexpensive, easily available, odourless, nontoxic, reusable and stable catalyst in many organic reactions.…”

Section: Introductionmentioning

confidence: 99%

Hofmann N‐alkylation of aniline derivatives with alcohols using ferric perchlorate immobilized on SiO₂ as a catalyst through Box–Behnken experimental design

Ghanimati

Abdoli‐Senejani

Isfahani

et al. 2018

Applied Organom Chemis

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Funding information Islamic Azad University-Arak BranchAn efficient method for the N-alkylation of poorly nucleophilic amines using ferric perchlorate immobilized on SiO 2 as a catalyst is described. Fe(ClO 4 ) 3 was prepared from mixing iron(III) hydroxide and perchloric acid and adsorbed on silica gel. The catalyst was characterized using various techniques. The supported ferric perchlorate (Fe(ClO 4 ) 3 /SiO 2 ) revealed high efficiency and selectivity for N-alkylation of aromatic amines with alcohols to provide alkylated amines. Various secondary amines were synthesized from primary amines and alcohols in good to excellent yields, with water as the only by-product. The optimization of the reaction conditions was investigated using the response surface method, and involving the Box-Behnken design matrix. The conditions for optimal reaction yield and time were: amount of catalyst = 0.34 mmol, temperature = 60°C and molar ratio of amine to alcohol = 1.2.The catalyst was recovered and reused for five cycles without a considerable decrease in catalytic activity. The stability of the recycled catalyst was investigated. The proposed method has numerous advantages including procedure simplicity, short reaction times, low cost, good to excellent yields, reusability of the catalyst and mild and environmentally benign conditions.

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Silica Gel Supported Ferric Perchlorate: A New and Efficient Reagent for One Pot Synthesis of Amides from Benzylic Alcohols

Cited by 27 publications

References 9 publications

Applications of Some Metal Hydrogen Sulfates in Organic Transformations

Applications of Some Metal Hydrogen Sulfates in Organic Transformations

Hydrated ferric perchlorate, Fe(ClO4)3.XH2O in organic synthesis. A short review

Hofmann N‐alkylation of aniline derivatives with alcohols using ferric perchlorate immobilized on SiO₂ as a catalyst through Box–Behnken experimental design

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Silica Gel Supported Ferric Perchlorate: A New and Efficient Reagent for One Pot Synthesis of Amides from Benzylic Alcohols

Cited by 27 publications

References 9 publications

Applications of Some Metal Hydrogen Sulfates in Organic Transformations

Applications of Some Metal Hydrogen Sulfates in Organic Transformations

Hydrated ferric perchlorate, Fe(ClO4)3.XH2O in organic synthesis. A short review

Hofmann N‐alkylation of aniline derivatives with alcohols using ferric perchlorate immobilized on SiO2 as a catalyst through Box–Behnken experimental design

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Product

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Hofmann N‐alkylation of aniline derivatives with alcohols using ferric perchlorate immobilized on SiO₂ as a catalyst through Box–Behnken experimental design