- One-pot thioetherification of aryl halides with thiourea and benzyl bromide in water catalyzed by Cu-grafted furfural imine-functionalized mesoporous SBA-15
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Surface functionalization of SBA-15 followed by its reaction with Cu(OAc)2 has been carried out to develop a new Cu-grafted functionalized mesoporous material, which catalyzes one-pot three component coupling of different aryl halides with thiourea and benzyl bromide in aqueous medium to produce aryl thioethers in very good yields (80-88%).
- Mondal, John,Modak, Arindam,Dutta, Arghya,Basu, Sohini,Jha,Bhattacharyya, Dibyendu,Bhaumik, Asim
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- A new Cu-anchored mesoporous organosilica material for facile C-S coupling reactions under microwave irradiation
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We report a new ordered Cu-anchored 2D-hexagonal mesoporous imine functionalized organosilica material Cu-MPIOS. This Cu-anchored mesoporous material has been synthesized via post synthetic functionalization of SBA-15 with 3-(2-aminoethylamino)propyl-dimethoxymethylsilane followed by Schiff-base condensation with 2-thiophene carboxaldehyde. Cu(I) has been grafted finally over Schiff-base functionalized mesoporous material through chemical impregnation to obtain Cu-MPIOS. The materials are characterized thoroughly using various techniques like powder X-ray diffraction, N2 adsorption/desorption analysis, FTIR, UV-vis spectroscopy, FEG-TEM, FE-SEM, 13C cross-polarization magic angle spinning NMR, TGA/DTA, EPR, AAS and CHN chemical analysis. High Brunauer-Emmett-Teller (BET) surface area and the presence of very large size mesopores (8.1 nm) in Cu-MPIOS has motivated us to explore its catalytic activity in one-pot three-component C-S cross coupling reaction by varying different aryl halides in the aqueous medium under microwave assisted heating conditions. This heterogeneous Cu-catalyst shows high catalytic performance as well as good recycling efficiency in this C-S coupling reaction, suggesting its future potential for the synthesis of value added thioether derivatives.
- Bhanja, Piyali,Gomes, Ruth,Satyanarayana, Lanka,Bhaumik, Asim
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- Functionalized graphene oxide as an efficient adsorbent for CO2 capture and support for heterogeneous catalysis
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We have designed new imine-functionalized graphene oxide (IFGO) through post synthetic modifications involving co-condensation of 3-aminopropyltriethoxysilane with graphene oxide basal plane containing hydroxyl and epoxy functional groups, followed by Schiff base condensation reaction with 2,6-diformyl-4-methylphenol and impregnation of copper(ii) to it through covalent attachment (Cu-IFGO). Powder X-ray diffraction, N2 sorption analysis, FT-IR, HR-TEM, FE-SEM and TGA/DTA analysis are employed to characterize the materials. The IFGO material exhibits good CO2 storage capacity of 8.10 mmol g-1 (35.64 wt%) and 2.10 mmol g-1 (9.24 wt%) at 273 K and 298 K temperature, respectively, up to 3 bar pressure, suggesting its potential application in environmental clean-up. Also, Cu-IFGO showed high catalytic activity in microwave-assisted one-pot three-component C-S coupling reactions for a diverse range of aryl halides with thiourea and benzyl bromide in aqueous medium to obtain aryl thioether products (maximum yield 86%), which are derivatives of natural products. Moreover, having imine and hydroxyl groups in functionalized graphene oxide, the grafted Cu(ii) chelated at the graphene oxide surface so strongly that it could not be leached out from the material during the course of the coupling reaction. Thus, it displayed very small decrease in product yield up to the sixth reaction cycle suggesting a sustainable future of this Cu(ii)-grafted catalyst.
- Bhanja, Piyali,Das, Sabuj Kanti,Patra, Astam K.,Bhaumik, Asim
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- Cu-grafted functionalized mesoporous SBA-15: A novel heterogeneous catalyst for facile one-pot three-component C-S cross-coupling reaction of aryl halides in water
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A highly ordered 2D hexagonal Cu-grafted functionalized mesoporous SBA-15 (Cu-PIF-SBA-15) has been designed through postsynthetic modification of mesoporous SBA-15. Surface functionalization technique has been employed to synthesize-NH2 functionalized mesoporous SBA-15 material. Schiff base condensation of this-NH2 functionalized SBA-15 with phloroglucinol dialdehyde leads to the formation of PIF-SBA-15. Reaction of PIF-SBA-15 with Cu(OAc)2·H2O in ethanol under reflux leads to the formation of Cu-PIF-SBA-15 catalyst. This Cu-PIF-SBA-15 catalyst exhibits excellent catalytic activity in a one-pot three-component C-S coupling reaction for a diverse range of aryl halides (bromide and chloride) with thiourea and benzyl bromide in aqueous medium to offer aryl alkyl thioether in very good yields. Due to the strong binding ability of the imine-N and phenolic-OH functional groups present in the phloroglucinol diimine moiety of the framework, the anchored Cu(II) could not leach out from the surface of the mesoporous catalyst during the course of reaction, and it has been observed that six repetitive reaction cycles could not cause any appreciable loss in the catalytic activity of this material.
- Mondal, John,Borah, Parijat,Modak, Arindam,Zhao, Yanli,Bhaumik, Asim
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p. 257 - 265
(2014/05/20)
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- A simple one-pot synthesis of hydroxylated and carboxylated aryl alkyl sulfides from various bromobenzenes
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A simple one-pot synthesis of aryl alkyl sulfides from various bromobenzenes containing a hydroxy, hydroxymethyl, hydroxyethyl, and carboxylic acid group at -o, -m, and -p positions is reported here. The reaction proceeds through, in sequence, in situ pro
- Ko, Jaeyoung,Ham, Jungyeob,Yang, Inho,Chin, Jungwook,Nam, Sang-Jip,Kang, Heonjoong
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p. 7101 - 7106
(2007/10/03)
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- Pd-mediated C-C and C-S bond formation on solid support: A scope and limitations study
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The scope and limitations of Pd(0)-mediated coupling reactions between aromatic halides linked to a polystyrene resin and boronic acid derivatives (Suzuki coupling), aromatic and vinylic tin compounds (Stille coupling), as well as thiols are reported. For all reactions, conditions were optimized and evaluated with various reagents. In many cases, upon cleavage from the solid support, products were obtained in excellent yields. In most cases, the optimized reaction conditions are superior to those previously reported in the literature.
- Wendeborn, Sebastian,Berteina, Sabine,Brill, Wolfgang K.-D.,De Mesmaeker, Alain
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p. 671 - 675
(2007/10/03)
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- Substituted alkylamine derivatives
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The substituted alkylamine derivatives represented by formula (I) STR1 wherein R1 represents (a) substituted or unsubstituted C2-6 alkenyl group, (b) substituted or unsubstituted C3-6 cycloalkenyl group, (c) substituted or unsubstituted C2-6 alkynyl group, (d) substituted or unsubstituted aryl group, (e) substituted or unsubstituted heterocyclic group, (f) fused heterocyclic group which may be substituted, or (g) group represented by the formula Ru11 -Ar wherein R11 is a heterocyclic group and Ar is a 5- or 6-membered aromatic ring which may contain a hetero N, O or S atom, and which may be substituted; STR2 represents a 5- or 6-membered aromatic ring which may contain a hetero N, O or S atom, and may be substituted by R7, X and Y are linking groups, R2 is H or lower alkyl, R3 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl or lower cycloalkyl, R4 and R5 are independently hydrogen or halogen atoms, R6 represents (a) substituted or unsubstituted acyclic hydrocarbon group which may be unsaturated, (b) substituted or unsubstituted cycloalkyl group, or (c) substituted or unsubstituted phenyl group, or non-toxic salts thereof. (E)-N-(6-6-dimethyl-2-hepten-4-ynyl)-N-ethyl-3-[4-(3-thienyl)-2-thienyl-methyloxy]benzylamine hydrochloride is a representative example. The substituted alkylamine derivatives are useful as pharmaceuticals, particularly for the treatment and prevention of hypercholesterolemia, hyperlipemia and arteriosclerosis.
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