One-Pot Synthesis of N-Arylated Amines by Hydroaminomethyl­ation of 2,5-Dihydrofuran with Aromatic Amines

Synthesis ◽  
2019 ◽  
Vol 51 (07) ◽  
pp. 1585-1594 ◽  
Author(s):  
Lailai Wang ◽  
Zhiwen Zheng
Keyword(s):  
Catalytic System ◽  
Catalyst Precursor ◽  
Reaction Parameters ◽  
Reaction Conditions ◽  
Phosphorus Ligands ◽  
One Pot ◽  
Cyclic Olefins ◽  
One Step ◽  
Important Intermediate ◽  
Optimal Reaction

A new efficient catalytic system for one-step synthesis of N-arylated amines, for example, an important intermediate, 4-ethyl-N-[(tetrahydrofuran-3-yl)methyl]aniline, is achieved by using different rhodium precursor and phosphorus ligands catalyzed hydroaminomethylation of aniline and its derivatives with heterocyclic and/or cyclic olefins. By screening the reaction parameters, the optimal reaction conditions are found as follows: methanol as a solvent, PPh3 as a ligand, [Rh(cod)2]BF4 as a catalyst precursor, a P/Rh ratio of 5:1, syngas pressure 4 MPa (H2/CO = 3:1), 100 °C, 20 hours, and no additives. The conversion of aniline reaches >99% and the yield of N-[(tetrahydrofuran-3-yl)methyl]aniline is up to 99% using this catalytic system. Moreover, the reaction of aniline and various cyclic olefins is investigated under the optimal conditions, and excellent conversion and good yields are obtained.

One-step chemoselective conversion of tetrahydropyranyl ethers to silyl-protected alcohols

RSC Advances ◽  
2014 ◽  
Vol 4 (28) ◽  
pp. 14475-14479 ◽  
Author(s):  
Julián Bergueiro ◽  
Javier Montenegro ◽  
Carlos Saá ◽  
Susana López
Keyword(s):  
Single Step ◽  
Protecting Groups ◽  
Reaction Conditions ◽  
One Pot ◽  
Silyl Ethers ◽  
Triple Bonds ◽  
Mild Conditions ◽  
Silyl Groups ◽  
One Step ◽  
Optimal Reaction

A novel chemoselective one-pot transformation of acetals to silyl ethers is reported. Free hydroxyls, double bonds and triple bonds are unaffected in optimal reaction conditions. This practical, inexpensive protocol allows the selective replacement of acetal-forming protecting groups with silyl groups in a single step under mild conditions.

Novel catalytic system: N-hydroxyphthalimide/hydrotalcite-like compounds catalysing allylic carbonylation of cyclic olefins

2016 ◽  
Vol 70 (7) ◽  
Author(s):  
Yin Zhou ◽  
Rui-Ren Tang ◽  
Dan Song
Keyword(s):  
Catalytic Activity ◽  
Reaction Mechanism ◽  
Catalytic System ◽  
Catalytic Reaction ◽  
Model Reaction ◽  
Reaction Conditions ◽  
Cyclic Olefins ◽  
Tert Butyl Hydroperoxide ◽  
Optimal Reaction ◽  
Catalytic Reaction Mechanism

Abstract-hydroxyphthalimide (NHPI) combined with stable and recoverable transition metal–aluminium binary hydrotalcite-like compounds (M-Al HTLcs, M = Cu, Ni, Co) as an unprecedented catalytic system was demonstrated for the allylic carbonylation, as the model reaction, of cyclic olefins with tert-butyl hydroperoxide (TBHP), using isophorone (IP) to ketoisophorone (KIP). The results showed NHPI combined with Cu-Al HTLcs to be an efficient catalytic system and the influences of various reaction conditions of the catalytic reaction were optimised. A maximum IP conversion of 68.0 % with 81.8 % selectivity to KIP was afforded under the optimal reaction conditions. Experiments of repeatability and restorability showed Cu-Al HTLcs to be stable for at least five cycles without noticeable loss of catalytic activity. Expanding substrates could also be efficiently converted to the corresponding ketones under the optimised reaction conditions with appreciable yields. A plausible catalytic reaction mechanism was proposed.

Conversion of Chitosan into 5-Hydroxymethylfurfural via Hydrothermal Synthesis

2015 ◽  
Vol 1095 ◽  
pp. 411-414 ◽  
Author(s):  
Jia Xuan Feng ◽  
Hong Jun Zang ◽  
Qing Yan ◽  
Ming Gaung Li ◽  
Bo Wen Cheng
Keyword(s):  
Aqueous Solution ◽  
Ionic Liquids ◽  
Hydrothermal Synthesis ◽  
Lewis Acids ◽  
Hydrothermal Condition ◽  
Hydrogen Sulfate ◽  
Reaction Parameters ◽  
Reaction Conditions ◽  
One Pot ◽  
Optimal Reaction

5-hydroxymethylfurfural (5-HMF) was produced from chitosan by a simple one-pot reaction including hydrolysis and dehydration in the presence of various ionic liquids and Lewis acids. Optimization of the reaction parameters including the screening of different catalysts, the effects of reaction time, temperature was investigated. The optimal reaction conditions are found to be 5 wt.% 1-butyl-3-methylimidazolium hydrogen sulfate ([BMIM][HSO4] ) aqueous solution and 100 mol% AlCl3•6H2O as cooperating catalyst, at 180 °C for 5 h under hydrothermal condition. HMF can be obtained in 25.2 % yield. More importantly, the catalysts can be recycled and exhibited constant activity for 5 successive trials.

Substoichiometric FeCl3 Activation of Propargyl Glycosides for the Synthesis of Disaccharides and Glycoconjugates

Synlett ◽  
2018 ◽  
Vol 29 (05) ◽  
pp. 668-672 ◽  
Author(s):  
Jianbo Zhang ◽  
Guosheng Sun ◽  
Yue Wu ◽  
Anqi Liu ◽  
Saifeng Qiu ◽  
...  
Keyword(s):  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
Optimal Reaction ◽  
Glycosyl Donors

Glycosides as glycosyl donors using FeCl3 have been described. Under optimal reaction conditions, three kinds of propargyl glycosides were found to react with steroids and sugar-derived glycosyl acceptors to afford the corresponding disaccharides and glycoconjugates in good to excellent yields (66–91%). Meanwhile, the method can also realize one-pot synthesis of disaccharides, making it an effective, affordable, and green glycosylation procedure.

Synthesis of Methacrolein by Condensation of Propionaldehyde with Formaldehyde

2011 ◽  
Vol 396-398 ◽  
pp. 1094-1097
Author(s):  
Yu Chao Li ◽  
Rui Yi Yan ◽  
Lei Wang ◽  
Lu Liu ◽  
Dan Liu ◽  
...  
Keyword(s):  
Methyl Methacrylate ◽  
Water Content ◽  
Atmospheric Pressure ◽  
Mannich Base ◽  
Amine Salt ◽  
Reaction Conditions ◽  
Starting Mixture ◽  
Important Intermediate ◽  
Polymer Dispersions ◽  
Optimal Reaction

Methacrolein is an important intermediate in the synthesis of methyl methacrylate (MMA), which is widely used for producing acrylic plastics or producing polymer dispersions for paints and coatings. In this paper, methacrolein was synthesized by condensation of propionaldehyde with formaldehyde in the pressense of amine salt through Mannich base intermediate at the atmospheric pressure. The optimal reaction conditions were obtained. The water content in starting mixture were also investigated

One-step Synthesis of β-lactams Using Cyanuric Fluoride

2013 ◽  
Vol 37 (1) ◽  
pp. 25-27 ◽  
Author(s):  
Maaroof Zarei
Keyword(s):  
Reaction Conditions ◽  
One Pot ◽  
Mild Conditions ◽  
One Pot Synthesis ◽  
One Step ◽  
Acetic Acids

Cyanuric fluoride works as an efficient acid activator reagent for the direct [2+2] ketene–imine cycloaddition of substituted acetic acids and imines in a one-pot synthesis under mild conditions. The yields are good to excellent and the reaction conditions are mild, simple and efficient.

scholarly journals One-Step Synthesis of Acylboron Compounds via Cu-Catalyzed Carbonylative Borylation of Alkyl Halides

2020 ◽  
Author(s):  
Cheng Li-Jie ◽  
Zhao Siling ◽  
Neal Mankad
Keyword(s):  
Alkyl Halides ◽  
Efficient Synthesis ◽  
Mechanistic Studies ◽  
Acyl Halide ◽  
Reaction Conditions ◽  
One Pot ◽  
One Step ◽  
High Yields ◽  
Tertiary Alkyl

A Cu-catalyzed carbonylative borylation of unactivated alkyl halides has been developed, enabling efficient synthesis of aliphatic potassium acyltrifluoroborates (KATs) in high yields by treating the in-situ formed tetracoordinated acylboron intermediates with aqueous KHF2. A variety of functional groups are tolerated under the mild reaction conditions, and primary, secondary and tertiary alkyl halides are all applicable. In addition, this method also provides facile access to N-methyliminodiacetyl (MIDA) acylboronates as well as α-methylated potassium acyltrifluoroborates in a one-pot manner. Mechanistic studies indicate a radical atom transfer carbonylation (ATC) mechanism to form acyl halide intermediates that are subsequently borylated by (NHC)CuBpin.<br>

scholarly journals Efficient Catalytic Production of Biodiesel with Acid-Base Bifunctional Rod-Like Ca-B Oxides by the Sol-Gel Approach

Materials ◽  
2018 ◽  
Vol 12 (1) ◽  
pp. 83 ◽  
Author(s):  
Anping Wang ◽  
Hu Li ◽  
Heng Zhang ◽  
Hu Pan ◽  
Song Yang
Keyword(s):  
Renewable Resources ◽  
Sol Gel ◽  
Acid Value ◽  
Catalytic Performance ◽  
Acid Base ◽  
Reaction Conditions ◽  
One Pot ◽  
Catalytic Material ◽  
Acid And Base ◽  
Optimal Reaction

The search for acid-base bifunctional catalysts has become a hot topic in the preparation of biofuels from renewable resources. In the present work, a series of novel acid-base bifunctional metal-boron catalysts were successfully prepared by a sol-gel method and characterized by XRD, IR, SEM, TEM, TGA, BET, and TPD. Among those bifunctional solid materials, the Ca-B(700) catalyst had the highest density of both acid and base sites and showed excellent catalytic performance in the production of biodiesel from nonedible oils with high acid value. Under the optimal reaction conditions of 20/1 methanol/oil mole ratio and 4 wt % catalyst dosage at 105 °C for 2 h, a high biodiesel yield of 96.0% could be obtained from Jatropha curcas oil in one-pot. In addition, Ca-B(700) was also applicable to producing biodiesel from Firmiana platanifolia L.f. oil in a relatively low acid value, with an almost quantitative yield (98.5%) at 65 °C after 2 h. The Ca-B(700) catalyst had good stability and reusability, which is a promising acid-base bifunctional catalytic material for the preparation of biodiesel.

Ligand-free Cu-catalyzed odorless synthesis of unsymmetrical sulfides through cross-coupling reaction of aryl/benzyl/alkyl halides with an aryl boronic acid/S8 system as a thiolating agent in PEG

RSC Advances ◽  
2015 ◽  
Vol 5 (46) ◽  
pp. 37060-37065 ◽  
Author(s):  
Abed Rostami ◽  
Amin Rostami ◽  
Arash Ghaderi ◽  
Mohammad Ali Zolfigol
Keyword(s):  
Boronic Acid ◽  
Coupling Reaction ◽  
Alkyl Halides ◽  
Green Solvent ◽  
Reaction Conditions ◽  
One Pot ◽  
Cross Coupling Reaction ◽  
Ligand Free ◽  
One Step ◽  
Aryl Boronic Acid

Efficient one-pot, one-step synthesis of unsymmetrical sulfides has been reported under mild reaction conditions with good yields in green solvent.

Study on the Reaction Characteristics of Directional Synthesis of α-Terpineol from Turpentine

2013 ◽  
Vol 634-638 ◽  
pp. 424-432 ◽  
Author(s):  
Yan Gu ◽  
Zhen Dong Zhao ◽  
Jie Song ◽  
Dong Mei Li ◽  
Jing Wang ◽  
...  
Keyword(s):  
High Purity ◽  
Theoretical Basis ◽  
Influence Factors ◽  
Separation Problem ◽  
Step Method ◽  
Reaction Conditions ◽  
Uniform System ◽  
Reaction Characteristics ◽  
One Step ◽  
Optimal Reaction

There was rarely high-purity α-terpineol or pure-monomer α-terpineol in China due to difficulty in isolating α-terpineol and γ-terpineol. Aiming at the separation problem, α-terpineol was directional synthesized by one-step method in a uniform system. The influence factors of stereochemistry structure, thermodynamic analysis and stability of reactants, products and carbocations were researched, conducting the experiments in optimal reaction conditions. All the influence factors about generating trend of objective product α-terpineol and byproduct γ-terpineol were discussed and the reaction mechanism was studied. This paper provided certain theoretical basis on prepare high-purity α-terpineol.

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