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• 3424-93-9 4-methoxyphenylacetamide 
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• 874-90-8 4-methoxybenzonitrile 

Relevant academic research and scientific papers

Fluorinated solvent-assisted photocatalytic aerobic oxidative amidation of alcoholsviavisible-light-mediated HKUST-1/Cs-POMoW catalysis

Considering the irreplaceable importance of photocatalytic functionalization reactions and the widespread attention paid to the use of metal-organic frameworks, especially their modified variants, for this purpose in recent years, different types of HKUST-1/POMoW composites were prepared through the immobilization of a series of Keggin-type polyoxometalates (POMs; POW = H3PW12O40, POMo = H3PMo12O40, and POMoW = H3PMo6W6O40) on HKUST-1 as a metal-organic framework (HKUST-1; Cu3(1,3,5-benzenetricarboxilicacid)2). Then, to produce HKUST-1/Cs-POM, the substitution of H+cations with Cs+ones as counter cations was carried out. The prepared composites were fully characterized with the PXRD (powder X-ray diffraction), FT-IR (Fourier transform infrared spectroscopy), BET and BJH (sorption of N2), TGA (thermo-gravimetric analysis), SEM (scanning electron microscopy), EDX (energy dispersive X-ray), TEM (transmission electron microscopy), UV-vis DRS (diffuse reflectance UV-vis spectroscopy), photoluminescence (PL) spectroscopy and ICP-AES (inductively coupled plasma atomic emission spectroscopy) techniques. The great importance?of the amide functional group and the attractiveness of photocatalytic oxidative functionalization?reactions led us to study the formation of this functional group using the prepared catalytic system in line with our previous research in this field. The HKUST-1/Cs-POMoW composite showed a raised photocatalytic performance compared to the discrete components, HKUST-1 and Cs-POMs, in aerobic oxidative amidation of alcohols under illumination with visible light, owing to the presence of catalytically active Cs-POMs deposited on the MOF particles. Besides, the combination of composite components mitigated the recombination rate of the electron-hole pairs, raising its photocatalytic activity. The attractiveness of fluorine solvents for oxidation reactions has led to the study of their role in the efficiency of oxidative amidation of alcohols and their significant effect on the efficiency of the process has been confirmed. The Cu-MOF/POM catalyst showed excellent stability during the reaction, and no significant decrease in its ability was observed during five consecutive cycles.

Metal-free approach for hindered amide-bond formation with hypervalent iodine(iii) reagents: application to hindered peptide synthesis

A new bio-inspired approach is reported for amide and peptide synthesis using α-amino esters that possess a potential activating group (PAG) at the ester residue. To activate the ester functionality under mild metal-free conditions, we exploited the facile dearomatization of phenols with hypervalent iodine(iii) reagents. Using a pyridine-hydrogen fluoride complex, highly reactive acyl fluoride intermediates can be successfully generated, thereby allowing for the smooth formation of sterically hindered amides and peptides from bulky amines and α-amino esters, respectively.

Oxidative amidation by Cu(ii)-guanidine acetic acid immobilized on magnetized sawdust with eggshell as a natural base

Copper(ii)-guanidine acetic acid complex was immobilized on the surface of magnetized raw waste sawdust (SD) as an abundant natural biopolymer and employed as an efficient and recoverable catalyst in oxidative amidation reaction, while waste eggshell (ES) powder was used as a low-cost solid base. The magnetic raw catalyst was fully characterized using FTIR, XRD, SEM, EDX, TGA, and VSM. A variety of amide derivatives were successfully synthesized in moderate to good yields using benzyl alcohol and amine salts. The application of sawdust and eggshell as two natural and abundant waste materials is the main advantage of this research. Moreover, these low-cost catalysts were recovered at least five times and utilized in reaction systems with a minimal decrease in activity.

Nickel/Briphos-Catalyzed Direct Transamidation of Unactivated Secondary Amides Using Trimethylsilyl Chloride

Direct transamidation of secondary amides was developed via nickel catalysis. In the presence of trimethylsilyl chloride and manganese, Ni(diglyme)Cl2 with a Briphos ligand efficiently promoted the transamidation of N-aryl benzamide derivatives with primary amines to afford the corresponding secondary amides in moderate to good yields. Primary amines bearing electron-donating groups gave higher yields of the transamidation products.

CuH-Catalyzed Asymmetric Hydroamidation of Vinylarenes

A CuH-catalyzed enantioselective hydroamidation reaction of vinylarenes has been developed using readily accessible 1,4,2-dioxazol-5-ones as electrophilic amidating reagents. This method provides a straightforward and efficient approach to synthesize chiral amides in good yields with high levels of enantiopurity under mild conditions. Moreover, this transformation tolerates substrates bearing a broad range of functional groups.

Air-stable Bis(pentamethylcyclopentadienyl) Zirconium Perfluorooctanesulfonate as an Efficient and Recyclable Catalyst for the Synthesis of N-substituted Amides

Bis(pentamethylcyclopentadienyl) zirconium perfluorooctanesulfonate is an air-stable and water-tolerant Lewis acid. This complex exhibited good thermal stability and high solubility in polar organic solvents. The compound showed relatively strong acidity, with an acid strength of 0.8Ho≤3.3, and high catalytic efficiency for the synthesis of N-substituted amides via the reaction of carboxylic acids with amines, the Ritter reaction of nitriles with alcohols, and the amination of alcohols with amides. Moreover, the complex had good reusability. This catalytic system affords a simple and efficient way to synthesize N-substituted amides.

Copper-amino group complexes supported on silica-coated magnetite nanoparticles: Efficient catalyst for oxidative amidation of methyl arenes

Magnetite nanoparticles coated with mesoporous silica, Fe3O4@SiO2, were prepared. Surface functionalization of this core-shell nanocomposite with (3-aminopropyl)trimethoxysilane (APTMS) followed by its reaction with Cu(OAc)2 was used to develop a new heterogeneous copper complex (Fe3O4@SiO2-APTMS-Cu). The structure and composition of the synthesized nanocatalyst were characterized by FTIR, SEM, VSM, TEM, XRD, and ICP analyses. The catalytic activity of the synthesized catalyst was probed in the oxidative amidation reaction of methyl arenes with amine hydrochloride salts. Various primary, secondary, and tertiary amides were prepared by this method. The magnetic properties of this catalyst lead to easy separation as well as providing significant catalyst recyclability. The catalyst is reusable 6 times without significant decrease in its catalytic activity.

An Unconventional Reaction of 2,2-Diazido Acylacetates with Amines

We have discovered that 2,2-diazido acylacetates, a class of compounds with essentially unknown reactivity, can be coupled to amines through a new strategy that does not involve any reagents. 2,2-Diazido acetate is the unconventional leaving group under carbon–carbon bond cleavage. This reaction leads to the construction of amide bonds, tolerates various functionalities and is performed equally well in numerous solvents under experimentally simple conditions. We also demonstrate that the isolation of the 2,2-diazido acylacetate compounds can be circumvented: Acylacetates were easily fragmented when treated with (Bu4N)N3 and iodine in the presence of an amine at room temperature. By using this method, a broad range of acylacetates with various structural motifs were directly transformed into amides.

One-Pot Synthesis of α-Branched N-Acylamines via Titanium-Mediated Condensation of Amides, Aldehydes, and Organometallics

A three-component, titanium-mediated synthesis of α-branched N-acylamines from commercial or readily accessible amides, aldehydes, and organometallic reagents is reported. The transformation proceeds under mild reaction conditions and tolerates a variety of functional groups (including nitrile, carbamate, olefin, basic amine, furan, and other sensitive heteroaromatics) to generate a large umbrella of α-branched N-acylamine products in high yields. The operationally practical procedure enables the use of this method in parallel chemical synthesis, a valuable feature that can facilitate the screening of bioactive molecules by medicinal chemists.

Copper-Catalyzed Reductive N-Alkylation of Amides with N-Tosylhydrazones Derived from Ketones

A CuI-catalyzed reductive coupling of ketone-derived N-tosylhydrazones with amides is presented. Under the optimized conditions, an array of N-tosylhydrazones derived from aryl–alkyl and diaryl ketones could couple effectively with a wide variety of (hete