Metal-organic framework Cu3 (BTC)2(H2O)3 catalyzed Aldol synthesis of pyrimidine-chalcone hybrids

Pathan, Naziyanaz B.; Rahatgaonkar, Anjali M.; Chorghade, Mukund S.

doi:10.1016/j.catcom.2011.03.040

Cited by 41 publications

(30 citation statements)

References 21 publications

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“…The poor stabilityo fM OFs makes them unsuitable for catalytic reruns.H owever, with advancements in post-synthesis modification techniques, it is possible for MOFs to be stabilized. Notably,K noevenagel condensation, [28] aldol condensation, [29] Suzuki-Miyaura coupling, [30] Ullmann coupling, [31] Sonogashira coupling, [32] Chan-Lam coupling, [33a] Mizoroki-Heck coupling, [34] Hantzchc oupling, [35] Glaser coupling, [36] Fischere sterification, [37] Friedel-Crafts' aroylation, [38] and aerobic oxidation [39] have all been demonstrated. Furthermore, the large open structures of MOFs ( Figure 2) enables smaller active metal nanoparticles (Table 1) and homogeneous catalysts to be incorporated into the framework, thereby making them useful for catalytic applications.…”

Section: Mofs As Catalystsmentioning

confidence: 99%

Engineering Metal–Organic Framework Catalysts for C−C and C−X Coupling Reactions: Advances in Reticular Approaches from 2014–2018

Kousik

Velmathi

2019

Chemistry A European J

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Metal-organic frameworks (MOFs) are ac lass of crystalline porousm aterials that have been activelyu sed for several industrial and synthetica pplications.M OFs are spatially and geometrically extrapolatedc oordination polymers with intriguing properties such as tunable porosity and dimensionality.Int erms of their catalytic efficiency,MOFs combine the easy recoverability of heterogeneous catalysts with the increased selectivity of biological catalysts. It is therefore not surprising that alot of work on optimizing MOF catalysts for organic transformationsh as been carriedo ut over the past decade. In this review,recent developments in MOF catalysis are summarized, with special attention being paid to CÀC, CÀN, and CÀOc oupling reactions. The influence of pore size, pore environment, and load on catalytic activity is described. Post-synthetics tabilization techniques and hostguest interactions in caged MOF scaffolds are detailed. Mechanistic aspects pertaining to the use of MOFs in asymmetric heterogeneousc atalysis are highlighted and categorized.

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Section: Mofs As Catalystsmentioning

confidence: 99%

Engineering Metal–Organic Framework Catalysts for C−C and C−X Coupling Reactions: Advances in Reticular Approaches from 2014–2018

Kousik

Velmathi

2019

Chemistry A European J

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“…[21][22][23] For those catalytic reactions where it is the metal cations integral to the MOF framework that are the catalytically active sites, the use of MOFs in Lewis acid-catalysed reactions has been particularly well-explored, especially for materials where coordinatively unsaturated sites can be generated throughout the pore space. Copper-bearing HKUST-1 [14,[24][25][26] and iron-and chromium-bearing MIL-100 and MIL-101, [27][28][29][30][31] for example, have been investigated extensively as Lewis acids, and much recent progress has been made in optimizing the zirconium terephthalate-based MOF, UiO-66 as a Lewis acid catalyst by defect manipulation and ligand functionalisation. [32,33] We recently introduced the scandium trimesate MIL-100(Sc) [34] into this arena of Lewis acid catalysis.…”

Section: Introductionmentioning

confidence: 99%

Mixed‐Metal MIL‐100(Sc,M) (M=Al, Cr, Fe) for Lewis Acid Catalysis and Tandem CC Bond Formation and Alcohol Oxidation

Mitchell¹,

Williamson²,

Ehrlichova³

et al. 2014

Chemistry A European J

108

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The trivalent metal cations Al(3+) , Cr(3+) , and Fe(3+) were each introduced, together with Sc(3+) , into MIL-100(Sc,M) solid solutions (M=Al, Cr, Fe) by direct synthesis. The substitution has been confirmed by powder X-ray diffraction (PXRD) and solid-state NMR, UV/Vis, and X-ray absorption (XAS) spectroscopy. Mixed Sc/Fe MIL-100 samples were prepared in which part of the Fe is present as α-Fe2 O3 nanoparticles within the mesoporous cages of the MOF, as shown by XAS, TGA, and PXRD. The catalytic activity of the mixed-metal catalysts in Lewis acid catalysed Friedel-Crafts additions increases with the amount of Sc present, with the attenuating effect of the second metal decreasing in the order Al>Fe>Cr. Mixed-metal Sc,Fe materials give acceptable activity: 40 % Fe incorporation only results in a 20 % decrease in activity over the same reaction time and pure product can still be obtained and filtered off after extended reaction times. Supported α-Fe2 O3 nanoparticles were also active Lewis acid species, although less active than Sc(3+) in trimer sites. The incorporation of Fe(3+) into MIL-100(Sc) imparts activity for oxidation catalysis and tandem catalytic processes (Lewis acid+oxidation) that make use of both catalytically active framework Sc(3+) and Fe(3+) . A procedure for using these mixed-metal heterogeneous catalysts has been developed for making ketones from (hetero)aromatics and a hemiacetal.

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“…[39] PbA C H T U N G T R E N N U N G (cpna) 2 ·2 DMF·6 H 2 O B A M N C H 3 CN r.t. [40] A [42] ZIF-8 BA MN toluene r.t. [43] ZIF-9 BA MN toluene r.t. [44] Pd [45] POM@MIL-101(Cr) BA ECA toluene 40 [46] PTA@MIL-101(Cr) BA 2-naphthol -90 [47] Tb-tca SA MN -r.t. [48] A [50] Condensation reactions catalyzed through proposed base catalysis ED-MIL-101(Cr) BA ECA C 6 H 12 80 [35] DETA-MIL-101(Cr) BA MN toluene r.t. [51] NH 2 -MIL-101(Cr) BA ECA toluene 60 [52] NH 2 -MIL-101(Al) BA ECA toluene 40 [53] NH 2 -MIL-101(Fe) BA MN toluene 80 [54] Zn [55] IRMOF-3 BA ECA DMF 40 [34] IRMOF-3 re-examination BA ECA ethanol 60 [56] SIM [59] Friedländer, Henry, aldol, Claisen-Schmidt and Pechmann condensation [61] Cu 3 A C H T U N G T R E N N U N G (btc) 2 APD FPD toluene 40 [62] FeA C H T U N G T R E N N U N G (btc) BA AP toluene 110 [63] MIL-101(Cr) acetone --180 [64] MIL-101-SO 3 H-NH 2 BADA NM -90 [65] CuA C H T U N G T R E N N U N G (padi) BADA MN DMSO-d 6 50 [66] A [68] UiO-66A C H T U N G T R E N N U N G (NH 2 ) BA heptanal -120 [69] Cu convenient from the environmental point of view considering the high biotoxicity of this metal. [39] PbA C H T U N G T R E N N U N G (cpna) 2 ·2 DMF·6 H 2 O B A M N C H 3 CN r.t. [40] A [42] ZIF-8 BA MN toluene r.t. [43] ZIF-9 BA MN toluene r.t. [44] Pd [45] POM@MIL-101(Cr) BA ECA toluene 40 [46] PTA@MIL-101(Cr) BA 2-naphthol -90 [47] Tb-tca SA MN -r.t. [48] A [50] Condensation reaction...…”

Section: Condensation Reactions Catalyzed Through Proposed Acid Catalmentioning

confidence: 99%

“…[62] The catalyst loading was tested and it was found that 11 mol% is required to give the maximum yield (87%) for 1 mmol of substrate. [62] The catalyst loading was tested and it was found that 11 mol% is required to give the maximum yield (87%) for 1 mmol of substrate.…”

Section: Aldol Condensationmentioning

confidence: 99%

Metal Organic Frameworks as Solid Catalysts in Condensation Reactions of Carbonyl Groups

et al. 2013

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This review summarizes the use of metal organic frameworks (MOFs) as solid catalysts for condensation reactions. After an introductory section, in which condensation reactions are generally presented, a list of the MOFs employed as condensation catalyst is given. The main part of the present review is organized according to the use of MOFs as solid acids, solid bases or as bi-functional solids containing both acid and basic sites. Throughout the review, the emphasis has been made on discussing the stability of the MOFs, their reusability and in providing a comparison of the performance of MOFs with respect to other homogeneous and heterogeneous catalysts. Finally, we summarize the current state-of-the-art and provide our view on future trends and developments in this field.

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Metal-organic framework Cu3 (BTC)2(H2O)3 catalyzed Aldol synthesis of pyrimidine-chalcone hybrids

Cited by 41 publications

References 21 publications

Engineering Metal–Organic Framework Catalysts for C−C and C−X Coupling Reactions: Advances in Reticular Approaches from 2014–2018

Engineering Metal–Organic Framework Catalysts for C−C and C−X Coupling Reactions: Advances in Reticular Approaches from 2014–2018

Mixed‐Metal MIL‐100(Sc,M) (M=Al, Cr, Fe) for Lewis Acid Catalysis and Tandem CC Bond Formation and Alcohol Oxidation

Metal Organic Frameworks as Solid Catalysts in Condensation Reactions of Carbonyl Groups

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