Chemoselective synthesis of long-chain alkyl-H-phosphinic acids via one-pot alkylation/oxidation of red phosphorus with alkyl-PEGs as recyclable micellar catalysts

Dibenzylamine motifs are an important class of crucial organic compounds and are widely used in fine chemical and pharmaceutical industries. The development of the efficient, economical, and environmentally friendly synthesis of amines using transition metal-based heterogeneous catalysts remains both desirable and challenging. Herein, we prepared the covalent organic framework (COF)-supported heterogeneous reduced COF-supported Pd-based catalyst and used it for the one-pot reductive amination of aldehydes. There are both Pd metallic state and oxidated Pdσ+ in the catalysts. Furthermore, in the presence of the reduced COF-supported Pd-based catalyst, many aromatic, aliphatic, and heterocyclic aldehydes with various functional groups substituted were converted to their corresponding amines products in good to excellent selectivity (up to 91%) under mild reaction conditions (70 °C, 2 h, NH3, 20 bar H2). This work expands the covalent organic frameworks for the material family and its support catalyst, opening up new catalytic applications in the economical, practical, and effective synthesis of secondary amines.

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One-pot, chemoselective synthesis of secondary amines from aryl nitriles using a PdPt–Fe3O4 nanoparticle catalyst

Catalysis Science & Technology ◽

10.1039/d0cy00630k ◽

2020 ◽

Vol 10 (13) ◽

pp. 4201-4209

Author(s):

Jin Hee Cho ◽

Sangmoon Byun ◽

Ahra Cho ◽

B. Moon Kim

Keyword(s):

Reductive Amination ◽

Secondary Amines ◽

Fe3o4 Nanoparticle ◽

Catalytic Method ◽

One Pot ◽

Chemoselective Synthesis ◽

Aryl Nitriles ◽

The One ◽

Nanoparticle Catalyst

We have developed a new catalytic method for the one-pot, cascade synthesis of unsymmetrical secondary amines via the reductive amination of aryl nitriles with nitroalkanes using a PdPt–Fe3O4 nanoparticle (NP) catalyst.

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Highly effective synthesis of 1-thioamidoalkyl-2-naphthols and tetrahydropyridines using a nanostructured silica-based catalyst under mild conditions

Combinatorial Chemistry & High Throughput Screening ◽

10.2174/1386207323666200914092345 ◽

2020 ◽

Vol 23 ◽

Author(s):

Navid Irannejad-Gheshlaghchaei ◽

Seyed Sajad Sajadikhah

Keyword(s):

Solvent Free ◽

One Pot ◽

Mild Conditions ◽

Solvent Free Conditions ◽

Highly Effective ◽

Effective Synthesis ◽

The One ◽

Yield Time ◽

High Yields ◽

Nanostructured Silica

Aim and Objective: Nano-2-[N',N'-dimethyl-N'-(silica-n-propyl)ethanaminium chloride]-N,N-dimethylaminium bisulfate (nano-[DSPECDA][HSO4]) was used as a highly effective and heterogeneous silica-based nanostructured catalyst for the synthesis of 1-thioamidoalkyl-2-naphthols and substituted tetrahydropyridines. Material and Methods: The expected products were prepared in mild conditions. In this work, three novel 1- thioamidoalkyl-2-naphthols and two new tetrahydropyridine derivatives were synthesized and characterized by IR, 1H and 13C NMR and Mass spectroscopy. Results: One-pot multi-component condensation of 2-naphthol with arylaldehydes and thioacetamide catalyzed by nano- [DSPECDA][HSO4] under green, mild and solvent-free conditions led to 1-thioamidoalkyl-2-naphthols in high yields. The nanocatalyst was also used for the preparation of functionalized tetrahydropyridines by the one-pot multi-component reaction of anilines, arylaldehydes and ethylacetoacetate under solvent-free and mild conditions. Conclusion: The reactions results are better compared to the literature in terms of one or more of these factors: yield, time, and the reaction media. All the products were purified by recrystallization from EtOH, and without column chromatography, which is good agreement with the green chemistry protocols.

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[Omim][BF4], a green and recyclable ionic liquid medium for the one-pot chemoselective synthesis of benzoxazinones

Tetrahedron Letters ◽

10.1016/j.tetlet.2010.01.122 ◽

2010 ◽

Vol 51 (14) ◽

pp. 1852-1855 ◽

Cited By ~ 18

Author(s):

Ali Sharifi ◽

Mehdi Barazandeh ◽

M. Saeed Abaee ◽

Mojtaba Mirzaei

Keyword(s):

Ionic Liquid ◽

Liquid Medium ◽

One Pot ◽

Chemoselective Synthesis ◽

The One ◽

Ionic Liquid Medium

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ChemInform Abstract: [Omim][BF4], a Green and Recyclable Ionic Liquid Medium for the One-Pot Chemoselective Synthesis of Benzoxazinones.

ChemInform ◽

10.1002/chin.201029181 ◽

2010 ◽

Vol 41 (29) ◽

pp. no-no

Author(s):

Ali Sharifi ◽

Mehdi Barazandeh ◽

M. Saeed Abaee ◽

Mojtaba Mirzaei

Keyword(s):

Ionic Liquid ◽

Liquid Medium ◽

One Pot ◽

Chemoselective Synthesis ◽

The One ◽

Ionic Liquid Medium

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A Series of Metal-Organic Frameworks for Selective CO2 Capture and Catalytic Oxidative Carboxylation of Olefins

10.26434/chemrxiv.7068509 ◽

2018 ◽

Author(s):

Huong T. D. Nguyen ◽

Y B. N. Tran ◽

Hung N. Nguyen ◽

Tranh C. Nguyen ◽

Felipe Gándara ◽

...

Keyword(s):

Room Temperature ◽

Gas Adsorption ◽

New Materials ◽

One Pot ◽

Acid Gas ◽

Naphthalene Diimide ◽

Styrene Carbonate ◽

Metal Organic ◽

Adsorption Of Co ◽

The One

Three novel lanthanide metal˗organic frameworks (Ln-MOFs), namely MOF-590, -591, and -592 were constructed from a naphthalene diimide tetracarboxylic acid. Gas adsorption measurements of MOF-591 and -592 revealed good adsorption of CO2 (low pressure, at room temperature) and moderate CO2 selectivity over N2 and CH4. Accordingly, breakthrough measurements were performed on a representative MOF-592, in which the separation of CO2 from binary mixture containing N2 and CO2 was demonstrated without any loss in performance over three consecutive cycles. Moreover, MOF-590, MOF-591, and MOF-592 exhibited catalytic activity in the one-pot synthesis of styrene carbonate from styrene and CO2 under mild conditions (1 atm CO2, 80 °C, and solvent-free). Among the new materials, MOF-590 revealed a remarkable efficiency with exceptional conversion (96%), selectivity (95%), and yield (91%).

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A Study on the Rearrangement of Dialkyl 1-Aryl-1-hydroxymethylphosphonates to Benzyl Phosphates

Current Organic Chemistry ◽

10.2174/1385272824666200226114306 ◽

2020 ◽

Vol 24 (4) ◽

pp. 465-471 ◽

Cited By ~ 2

Author(s):

Zita Rádai ◽

Réka Szabó ◽

Áron Szigetvári ◽

Nóra Zsuzsa Kiss ◽

Zoltán Mucsi ◽

...

Keyword(s):

Quantum Chemical ◽

Room Temperature ◽

Phase Transfer ◽

One Pot ◽

Substrate Dependence ◽

Triethylbenzylammonium Chloride ◽

One Step ◽

The Pudovik Reaction ◽

The One ◽

Solid Liquid

The phospha-Brook rearrangement of dialkyl 1-aryl-1-hydroxymethylphosphonates (HPs) to the corresponding benzyl phosphates (BPs) has been elaborated under solid-liquid phase transfer catalytic conditions. The best procedure involved the use of triethylbenzylammonium chloride as the catalyst and Cs2CO3 as the base in acetonitrile as the solvent at room temperature. The substrate dependence of the rearrangement has been studied, and the mechanism of the transformation under discussion was explored by quantum chemical calculations. The key intermediate is an oxaphosphirane. The one-pot version starting with the Pudovik reaction has also been developed. The conditions of this tandem transformation were the same, as those for the one-step HP→BP conversion.

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An Overview of the One-pot Synthesis of Imidazolines

Current Organic Chemistry ◽

10.2174/1385272824999201001153735 ◽

2020 ◽

Vol 24 (20) ◽

pp. 2341-2355

Author(s):

Thaipparambil Aneeja ◽

Sankaran Radhika ◽

Mohan Neetha ◽

Gopinathan Anilkumar

Keyword(s):

Asymmetric Catalysis ◽

Organic Compounds ◽

Ring Opening ◽

Ecological Impact ◽

Chiral Auxiliary ◽

One Pot ◽

One Pot Synthesis ◽

The One ◽

Synthetic Intermediate ◽

Heterocyclic Moiety

One-pot syntheses are a simple, efficient and easy methodology, which are widely used for the synthesis of organic compounds. Imidazoline is a valuable heterocyclic moiety used as a synthetic intermediate, chiral auxiliary, chiral catalyst and a ligand for asymmetric catalysis. Imidazole is a fundamental unit of biomolecules that can be easily prepared from imidazolines. The one-pot method is an impressive approach to synthesize organic compounds as it minimizes the reaction time, separation procedures, and ecological impact. Many significant one-pot methods such as N-bromosuccinimide mediated reaction, ring-opening of tetrahydrofuran, triflic anhydrate mediated reaction, etc. were reported for imidazoline synthesis. This review describes an overview of the one-pot synthesis of imidazolines and covers literature up to 2020.

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Synthesis and Kinetics of Highly Substituted Piperidines in the Presence of Tartaric Acid as a Catalyst

Combinatorial Chemistry & High Throughput Screening ◽

10.2174/1386207321666180228115130 ◽

2018 ◽

Vol 21 (4) ◽

pp. 302-311

Author(s):

Younes Ghalandarzehi ◽

Mehdi Shahraki ◽

Sayyed M. Habibi-Khorassani

Keyword(s):

Ambient Temperature ◽

Tartaric Acid ◽

Aromatic Aldehydes ◽

One Pot ◽

Rate Determining Step ◽

State Approximation ◽

Solvent Free Conditions ◽

Steady State Approximation ◽

Absorbance Changes ◽

The One

Aim & Scope: The synthesis of highly substituted piperidine from the one-pot reaction between aromatic aldehydes, anilines and β-ketoesters in the presence of tartaric acid as a catalyst has been investigated in both methanol and ethanol media at ambient temperature. Different conditions of temperature and solvent were employed for calculating the thermodynamic parameters and obtaining an experimental approach to the kinetics and mechanism. Experiments were carried out under different temperature and solvent conditions. Material and Methods: Products were characterized by comparison of physical data with authentic samples and spectroscopic data (IR and NMR). Rate constants are presented as an average of several kinetic runs (at least 6-10) and are reproducible within ± 3%. The overall rate of reaction is followed by monitoring the absorbance changes of the products versus time on a Varian (Model Cary Bio- 300) UV-vis spectrophotometer with a 10 mm light-path cell. Results: The best result was achieved in the presence of 0.075 g (0.1 M) of catalyst and 5 mL methanol at ambient temperature. When the reaction was carried out under solvent-free conditions, the product was obtained in a moderate yield (25%). Methanol was optimized as a desirable solvent in the synthesis of piperidine, nevertheless, ethanol in a kinetic investigation had none effect on the enhancement of the reaction rate than methanol. Based on the spectral data, the overall order of the reaction followed the second order kinetics. The results showed that the first step of the reaction mechanism is a rate determining step. Conclusion: The use of tartaric acid has many advantages such as mild reaction conditions, simple and readily available precursors and inexpensive catalyst. The proposed mechanism was confirmed by experimental results and a steady state approximation.

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