87069-72-5Relevant academic research and scientific papers
Fluorinated solvent-assisted photocatalytic aerobic oxidative amidation of alcoholsviavisible-light-mediated HKUST-1/Cs-POMoW catalysis
Azarkhosh, Zahra,Heydari, Akbar,Karimi, Meghdad,Mahjoub, Alireza,Mohebali, Haleh,Sadeghi, Samira,Safarifard, Vahid
supporting information, p. 14024 - 14035 (2021/08/16)
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.
Green synthesis of primary, secondary, and tertiary amides through oxidative amidation of methyl groups with amine hydrochlorides over recyclable CoFe2O4 NPs
Eidi, Esmaiel,Kassaee, Mohammad Zaman
, p. 106873 - 106879 (2016/11/23)
A practical and efficient method is developed for efficient synthesis of a wide variety of 1°, 2°, and 3° amides through amidation of methylarenes with amine hydrochloride salts, over magnetic CoFe2O4 NPs as a recyclable nanocatalyst, and aqueous tert-butyl hydroperoxide as an oxidant. This economically sound amidation reaction is operationally straightforward and provides desired amides in good to excellent yields, under mild conditions.
Superparamagnetic Fe(OH)3@Fe3O4 nanoparticles: An efficient and recoverable catalyst for tandem oxidative amidation of alcohols with amine hydrochloride salts
Arefi, Marzban,Saberi, Dariush,Karimi, Meghdad,Heydari, Akbar
supporting information, p. 341 - 347 (2015/06/22)
Magnetic Fe(OH)3@Fe3O4 nanoparticles were successfully prepared and characterized. This magnetic nanocomposite was employed as an efficient, reusable, and environmentally benign heterogeneous catalyst for the direct amidation of alcohols with amine hydrochloride salts. Several derivatives of primary, secondary and tertiary amides were synthesized in moderate to good yields in the presence of this catalytic system. The catalyst was successfully recycled and reused up to six times without significant loss of its catalytic activity.
Direct oxidative amidation of benzyl alcohols using EDTA@Cu(II) functionalized superparamagnetic nanoparticles
Azizi, Kobra,Karimi, Meghdad,Nikbakht, Fatemeh,Heydari, Akbar
, p. 336 - 343 (2014/07/21)
Superparamagnetic Fe3O4@EDTA-Cu(II) nanoparticles were readily prepared and identified as an effective catalyst for the tandem transformation of benzyl alcohols and amine hydrochloride salts into the corresponding amides with tert-bu
Oxidative amidation of aromatic aldehydes with amine hydrochloride salts catalyzed by silica-coated magnetic carbon nanotubes (MagCNTs@SiO 2)-immobilized imine-Cu(I)
Saberi, Dariush,Heydari, Akbar
, p. 101 - 108 (2014/02/14)
Mesoporous silica-coated magnetic carbon nanotubes were prepared; their surface functionalization, followed by reaction with CuI, were carried out to develop a Cu-grafted functionalized mesoporous material. This system is able to catalyze oxidative amidation of aromatic aldehydes with amine hydrochloride salts, generating amide derivatives in moderate to good yields. Magnetic properties of this catalyst led to easy separation as well as providing significant recyclability.
Selective amidation of 2,6-dihalogenopurines: Application to the synthesis of new 2,6,9-trisubstituted purines
Piguel, Sandrine,Legraverend, Michel
, p. 7026 - 7029 (2008/02/11)
(Chemical Equation Presented) We report herein the palladium(0)/Xantphos- catalyzed cross-coupling of various amides with 2,6-dihalogenopurines, with substituent-dependent regioselectivity. Furthermore, subjecting the same 2,6-dihalogenopurines to SN
Combining Magnetic Resonance Spectroscopies, Mass Spectrometry, and Molecular Dynamics: Investigation of Chiral Recognition by 2,6-di-O-Methyl-β-cyclodextrin
Franchi, Paola,Lucarini, Marco,Mezzina, Elisabetta,Pedulli, Gian Franco
, p. 4343 - 4354 (2007/10/03)
EPR spectroscopy has been employed to investigate the formation of complexes between heptakis-(2,6-O-dimethyl)-β-cyclodextrin (DM-β-CD) and different enantiomeric pairs of chiral nitroxides of general structure PhCH2N(O·)CH(R)R′. Accurate equilibrium measurements of the concentrations of free and included radicals afforded the binding constant values for these nitroxides. The relationship between the stereochemistry of the DM-β-CD complexes and the thermodynamics of complexation was elucidated by correlating EPR data with 1H-1H NOE measurements carried out on the complexes between DM-β-CD and the structurally related amine precursors of nitroxides. NOE data suggested that inclusion of the stereogenic center in the DM-β-CD cavity occurs only when the R substituent linked to the chiral carbon contains an aromatic ring. For these types of complexes, molecular dynamics simulation indicated that the depth of penetration of the stereogenic center into the cyclodextrin cavity is determined by the nature of the second substituent (R′) at the asymmetric carbon and is responsible for the observed chiral selectivity. Analysis of mass spectra showed that, for the presently investigated amines, electrostatic external adducts of CDs with protonated amines are detected by ESI-MS.
Synthesis and oxidation of chiral 2-thiazolines (4,5-dihydro-1,3-thiazoles)
Aitken, R. Alan,Armstrong, David P.,Galt, Ronald H. B.,Mesher, Shaun T. E.
, p. 935 - 943 (2007/10/03)
Eight new chiral 2-thiazolines (4,5-dihydro-1,3-thiazoles) 2 have been prepared by treatment of the 2-methyloxazolines 1, the benzoylamino alcohols 4 or the trimethylacetylamino alcohols 5 with P2S5. With a 2-methyl substituent, reaction with Oxone results in ring-opening to give the acetylamino disulfides 9 and with MCPBA there is also ring-opening with incorporation of a m-chlorobenzoyl group to give 12. Treatment of the 2-phenyl compounds with a variety of oxidants gives the benzoylamino sulfonic acids 10 and the disulfides 9 together with the thiazoles 11 in varying proportions. The sulfonic acids and thiazoles are obtained in pure form by reaction with 3 equiv. of peracetic acid and with sulfur, respectively. Although reaction of 2d-f with KMnO4 under phase-transfer conditions gives the thiazoles 11, addition of 1 equiv. of benzoic acid results in a complete change in selectivity to afford the thiazoline 1,1-dioxides 3d-f in excellent yield. These compounds prove to be exceptionally moisture-sensitive and readily hydrolyse to give the benzoylamino sulfinic acids 8 whose further oxidation and disproportionation probably explains the formation of the sulfonic acids and disulfides with the other oxidants. The high reactivity of the sulfones 3 towards nucleophilic ring-opening precludes their deprotonation and alkylation. Upon flash vacuum pyrolysis at 600°C, they fragment to give SO2, benzonitrile and the alkenes 16 in high yield. Fully assigned 13C NMR spectra are presented for the 18 heterocyclic compounds prepared and for 17 acyclic derivatives.
