65608-94-8Relevant articles and documents
An insight into the synthesis, crystal structure, geometrical modelling of crystal morphology, Hirshfeld surface analysis and characterization of N-(4-methylbenzyl)benzamide single crystals
Goel, Sahil,Yadav, Harsh,Singh, Nidhi,Singh, Budhendra,Bdikin, Igor,Rao, Devarapalli Chenna,Gopalaiah, Kovuru,Kumar, Binay
, p. 1498 - 1511 (2017)
A versatile approach for the synthesis of N-(4-methylbenzyl)benzamide, C15H15NO, using CuI as catalyst has been reported. Single crystals of the synthesized compound were grown using the slow evaporation solution technique. The crystal structure of the N-(4-methylbenzyl)benzamide crystals has been determined by single-crystal X-ray diffraction. The compound crystallizes in an orthorhombic lattice, noncentrosymmetric space group Pna21. The crystal structure is stabilized by intermolecular N-H?O hydrogen bonds and weak C-H?π interactions to form layers parallel to the a axis. A user-friendly approach based on centre of mass propagation vector theory was used to predict the crystal morphology. The framework developed here utilizes the concept of intermolecular bond strength to discern the crystal morphology. Fourier transform IR, NMR and high-resolution mass spectrometry analytical techniques were used for the identification of functional groups and confirmation of the structure of the title compound. All of the intermolecular interactions present in the crystal structure, including the C-H?π, C-H?O and N-H?O interactions, were investigated and confirmed by molecular Hirshfeld surface analysis. From linear optical spectroscopy, the transmittance, optical band gap and UV cutoff wavelength were determined. The photoluminescence emission spectrum was recorded for a grown crystal. Dielectric measurements were performed at room temperature for various frequencies. The mechanical strength of the (001) plane of the title compound was measured using the Vickers micro-hardness technique. A piezo-coefficient of 15pCN-1 was found along the (001) plane of the title crystals. The thermal stability and melting point were also investigated. In addition, density functional theory simulations were used to calculate the optimized molecular geometry and the UV-vis spectrum, and to determine the highest occupied molecular orbital/lowest unoccupied molecular orbital energy gap. The results show that N-(4-methylbenzyl)benzamide is a potential candidate for multifunctional optical and piezoelectric crystals.
Silver-Catalyzed Hydroboration of C-X (X = C, O, N) Multiple Bonds
Pandey, Vipin K.,Tiwari, Chandra Shekhar,Rit, Arnab
supporting information, p. 1681 - 1686 (2021/03/03)
AgSbF6 was developed as an effective catalyst for the hydroboration of various unsaturated functionalities (nitriles, alkenes, and aldehydes). This atom-economic chemoselective protocol works effectively under low catalyst loading, base- A nd solvent-free moderate conditions. Importantly, this process shows excellent functional group tolerance and compatibility with structurally and electronically diverse substrates (>50 examples). Mechanistic investigations revealed that the reaction proceeds via a radical pathway. Further, the obtained N,N-diborylamines were showcased to be useful precursors for amide synthesis.
Acetonitrile and benzonitrile as versatile amino sources in copper-catalyzed mild electrochemical C-H amidation reactions
Budnikova, Yulia,Kononov, Alexander,Rizvanov, Ildar,Strekalova, Sofia
, p. 37540 - 37543 (2021/12/07)
A mild, efficient electrochemical approach to the site-selective direct C-H amidation of benzene and its derivatives with acetonitrile and benzonitrile has been developed. It has been shown that joint electrochemical oxidation of various arenes in the presence of a copper salt as a catalyst and nitriles leads to the formation of N-phenylacetamide from benzene and N-benzylacetamides from benzyl derivatives (up to 78% yield). A favorable feature of the process is mild conditions (room temperature, ambient pressure, no strong oxidants) that meet the criteria of green chemistry.
Reductive N-alkylation of primary amides using nickel-nanoparticles
Alenad, Asma M.,Alshammari, Ahmad S.,Jagadeesh, Rajenahally V.,Murugesan, Kathiravan,Sohail, Manzar
, (2021/11/22)
Here we report Ni-nanoparticles as reusable catalysts for reductive N-alkylation of amides. These Ni-nanoparticles based catalysts have been prepared by the template synthesis of tartaric acid and 2-methyl imidazole ligated Ni-complex on SiO2 and subsequent pyrolysis under argon. Applying optimal Ni-nanostructured catalyst, N-alkylation of aromatic and heterocyclic primary amides with different aldehydes in presence of molecular hydrogen was performed to access structurally diverse N-alkylated amides in good to excellent yields. In addition, the applicability of this N-alkylation protocol has been demonstrated for the selective functionalization of primary amide group in Levetiracetam drug.
Dehydrogenative amide synthesis from alcohols and amines utilizing N-heterocyclic carbene-based ruthenium complexes as efficient catalysts: The influence of catalyst loadings, ancillary and added ligands
Wang, Wan-Qiang,Wang, Zhi-Qin,Sang, Wei,Zhang, Rui,Cheng, Hua,Chen, Cheng,Peng, Da-Yong
, (2021/01/05)
The metal-catalyzed dehydrogenative coupling of alcohols and amines to access amides has been recognized as an atom-economic and environmental-friendly process. Apart from the formation of the amide products, three other kinds of compounds (esters, imines and amines) may also be produced. Therefore, it is of vital importance to investigate product distribution in this transformation. Herein, N-heterocyclic carbene-based Ru (NHC/Ru) complexes [Ru-1]-[Ru-5] with different ancillary ligands were prepared and characterized. Based on these complexes, we selected condition A (without an added NHC precursor) and condition B (with an added NHC precursor) to comprehensively explore the selectivity and yield of the desired amides. After careful evaluation of various parameters, the Ru loadings, added NHC precursors and the electronic/steric properties of ancillary NHC ligands were found to have considerable influence on this catalytic process.
Direct synthesis of amides and imines by dehydrogenative homo or cross-coupling of amines and alcohols catalyzed by Cu-MOF
Anbardan, Soheil Zamani,Bozcheloei, Abolfazl Hassani,Mokhtari, Javad,Yari, Ahmad
, p. 20788 - 20793 (2021/07/01)
Oxidative dehydrogenative homo-coupling of amines to imines and cross-coupling of amines with alcohols to amides was achieved with high to moderate yields at room temperature in THF using Cu-MOF as an efficient and recyclable heterogeneous catalyst under mild conditions. Different primary benzyl amines and alcohols could be utilized for the synthesis of a wide variety of amides and imines. The Cu-MOF catalyst could be recycled and reused four times without loss of catalytic activity.
Half-Sandwich Ruthenium Complexes Bearing Hemilabile κ2-(C,S)?Thioether-Functionalized NHC Ligands: Application to Amide Synthesis from Alcohol and Amine
Achard, Thierry,Bellemin-Laponnaz, Stéphane,Chen, Weighang,Egly, Julien,Maisse-Fran?ois, Aline
supporting information, (2022/01/20)
Amide synthesis is one of the most crucial transformations in chemistry and biology. Among various catalytic systems, N-heterocyclic carbene (NHC)-based ruthenium (Ru) catalyst systems have been proven to be active for direct synthesis of amides by sustainable acceptorless dehydrogenative Coupling of primary alcohols with amines. Most often, these catalytic systems usually use monodentate NHC and thus require an additional ligand to obtain high reactivity and selectivity. In this work, a series of cationic Ru(II)(η6-p-cymene) complexes with thioether-functionalized N-heterocyclic carbene ligands (imidazole and benzimidazole-based) have been prepared and fully characterized. These complexes have then been used in the amidation reaction and the most promising one (i. e. 3 c) has been applied on a large range of substrates. High conversions albeit with moderate yields have generally been obtained.
Graphene oxide: A convenient metal-free carbocatalyst for facilitating amidation of esters with amines
Patel, Khushbu P.,Gayakwad, Eknath M.,Shankarling, Ganapati S.
, p. 2661 - 2668 (2020/02/20)
Herein, we report a graphene oxide (GO) catalyzed condensation of non-activated esters and amines, that can enable diverse amides to be synthesized from abundant ethyl esters forming only volatile alcohol as a by-product. GO accelerates ester to amide conversion in the absence of any additives, unlike other catalysts. A wide range of ester and amine substrates are screened to yield the respective amides in good to excellent yields. The improved catalytic activity can be ascribed to the oxygenated functionalities present on the graphene oxide surface which forms H-bonding with the reactants accelerating the reaction. Improved yields and a wide range of functional group tolerance are some of the important features of the developed protocol.
The synthesis and structure of pyridine-oxadiazole iridium complexes and catalytic applications: Non-coordinating-anion-tuned selective C–N bond formation
Yao, Wei,Zhang, Yilin,Zhu, Haiyan,Ge, Chenyang,Wang, Dawei
, p. 701 - 705 (2019/09/30)
Several novel pyridine-oxadiazole iridium complexes were synthesized and characterized through X-ray crystallography. The designed iridium complexes revealed surprisingly high catalytic activity in C–N bondformation of amides and benzyl alcohols with the assistance of non-coordinating anions. In an attempt to achieve borrowing hydrogen reactions of amides with benzyl alcohols, N,N'-(phenylmethylene)dibenzamide products were unexpectedly isolated under non-coordinating anion conditions, whereas N-benzylbenzamide products were achieved in the absence of non-coordinating anions. The mechanism explorations excluded the possibility of “silver effect” (silver-assisted or bimetallic catalysis) and revealed that the reactivity of iridium catalyst was varied by non-coordinating anions. This work provided a convenient and useful methodology that allowed the iridium complex to be a chemoselective catalyst and demonstrated the first example of non-coordinating-anion-tuned selective C–N bond formation
An unprecedented cobalt-catalyzed selective aroylation of primary amines with aroyl peroxides
Li, Dong,Li, Jiale,Li, Juanjuan,Yuan, Songdong,Zhang, Qian
supporting information, (2020/09/16)
A novel and facile cobalt-catalyzed selective aroylation of primary amines with aroyl peroxides was developed for the synthesis of aryl amides. It was unprecedented that C[sbnd]N bond formation product was selectively generated without the common N[sbnd]O bond formation product. Aroyl peroxides act as the sole aroylation reagent without additional base or oxidant. The reactions proceeded under mild conditions and showed broad substrates scope with a series of primary amines and aroyl peroxides.
