A chiral metal–organic framework for sequential asymmetric catalysis

Song, Feijie; Wang, Cheng; Lin, Wenbin

doi:10.1039/c1cc12701b

Cited by 176 publications

(100 citation statements)

References 37 publications

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“…Nevertheless, the inherent instability of the CMOFs (7.5% Mn leaching) limits their use in enantioselective epoxidation reactions. In another recent work of Lin a different Mn(salen) ligand was applied to synthesize a chiral MOF having the same SBU as in one of their previous works (entry 1, Table 5) 125 which was the first MOF catalyzing sequential alkene epoxidation/epoxide ring-opening reactions.…”

Section: Mofs In Chiral Oxidation Catalysismentioning

confidence: 99%

Metal-Organic Frameworks as Selective or Chiral Oxidation Catalysts

2014

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Since the discovery of Metal Organic Frameworks (MOFs) in the early 1990, the amount of new structures has grown exponentially. A MOF typically consists of inorganic nodes that are connected by organic linkers to form crystalline, highly porous structures. MOFs have attracted a lot of attention lately, as the versatile design of such materials holds promises of interesting applications in various fields. In this review, we will focus on the use of MOFs as heterogeneous oxidation catalysts. MOFs are very promising candidates to replace homogeneous catalysts by sustainable and stable heterogeneous catalysts. The catalytic active function can be either the active metal sites of the MOF itself or can be introduced as an extra functionality in the linker, a dopant or a "ship-in-a-bottle" complex. As the pore size, pore shape and functionality of MOFs can be designed in numerous ways, shape selectivity and even chiral selectivity can be created. In this review, we will present an overview on the state of the art of the use of MOFs as a heterogeneous catalyst in liquid phase oxidation reactions.

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Section: Mofs In Chiral Oxidation Catalysismentioning

confidence: 99%

Metal-Organic Frameworks as Selective or Chiral Oxidation Catalysts

2014

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“…Catalytic activities of CMOF-1 and CMOF-6 towards asymmetric epoxidation were evaluated with 2-(t-butylsulphonyl)iodosylbenzene as the oxidant and aromatic substituted olefins as the substrates (Song et al 2010(Song et al , 2011. As shown in table 1, the MOF-catalysed reaction gave good to excellent yields and moderate to good ees which are comparable with the homogeneous controls.…”

Section: (B) Asymmetric Epoxidation Catalysismentioning

confidence: 72%

“…• C (Song et al 2011). As determined by single-crystal X-ray crystallography, CMOF-6 crystallizes in the trigonal R3 space group with the asymmetric unit of four L 4 ligands and four-third of the Zn 4 (m 4 -O) clusters.…”

Section: Results and Discussion (A) Synthesis And Structural Charactermentioning

confidence: 99%

“…The whole structure can be described as a close packing of seven-node cages constructed from three pentagonal faces and a triangular face (figure 4). Adopting a twofold interpenetrated structure, CMOF-6 exhibits triangular open channels with the edge length of 2.9 nm and a void space of 87.8 per cent (Song et al 2011). Compared with the IRMOF framework CMOF-1, CMOF-6 exhibits higher solvent weight loss (70.5% versus 50.0%) and dye uptake (70.5 versus 14.5 wt% for Brilliant Blue R-250), verifying the larger open channel sizes and higher porosity of CMOF-6 than CMOF-1 as shown in the structural models.…”

Section: Results and Discussion (A) Synthesis And Structural Charactermentioning

confidence: 99%

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Chiral porous metal-organic frameworks with dual active sites for sequential asymmetric catalysis

et al. 2012

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Metal-organic frameworks (MOFs) are a class of organic-inorganic hybrid materials built from metal-connecting nodes and organic-bridging ligands. They have received much attention in recent years owing to the ability to tune their properties for potential applications in various areas. Properly designed MOFs with uniform, periodically aligned active sites have shown great promise in catalysing shape-, size-, chemo-, regio-and stereo-selective organic transformations. This study reports the synthesis and characterization of two chiral MOFs (CMOFs 1 and 2) that are constructed from Mn-salen-derived dicarboxylic acids [salen 8 ] secondary building units (SBUs), respectively. The SBUs in CMOF-1 are connected by the linear ditopic Mn-salen-derived linkers to construct a fourfold interpenetrated isoreticular MOF (IRMOF) structure with pcu topology. In CMOF-2, the Mnsalen centres dimerize in a cross-linking way to form a diamondoid structure with threefold interpenetration. CMOF-1 was examined for highly regio-and stereo-selective tandem alkene epoxidation/epoxide ring-opening reactions by using the Mn-salen and Zn 4 (m 4 -O)(carboxylate) 6 active sites, respectively. Our work demonstrated the potential utility of chiral MOFs with multiple active sites in the efficient synthesis of complex molecules with excellent regio-and stereo-controls

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“…The asymmetric epoxidation catalysed by the chiral Mn unit was followed by ring opening catalysed by the Zn species found in the secondary building unit of the MOF, with preservation of the molecule chirality. 136 Chiral titanium metal-organic assemblies were prepared from BINOL/Salalen or BINOL/Salan heteroditopic ligands. These materials were used in the sequential epoxidation of a cyclic olefin 57 with H 2 O 2 , followed by the stereoselective ring-opening of the resulting meso-epoxide to hydroxylamine 59 using benzylamine (58) (Scheme 18b).…”

Section: View Article Onlinementioning

confidence: 99%

Asymmetric one-pot reactions using heterogeneous chemical catalysis: recent steps towards sustainable processes

Szőllősi

2018

Catal. Sci. Technol.

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The preparation of optically pure fine chemicals is among the most important and challenging tasks met by organic chemists. Recently, significant efforts have been focused on the development of green and sustainable procedures for the synthesis of these high value-added compounds. Asymmetric heterogeneous catalysis has provided efficient solutions to these challenges. The application of heterogeneous chiral catalysts in one-pot processes combines the advantages of use of these materials with time, material, and energy savings associated with cascade or sequential procedures. This review surveys these asymmetric onepot reactions reported until July 2017, in which a heterogeneous chemical catalyst has been applied either as a single multifunctional catalyst or in combination with a second catalytically active material. These processes include one-pot procedures catalysed by carefully designed solids obtained by the immobilization of chiral metal complexes, by anchoring chiral organocatalysts, or by modifying catalytic surfaces with optically pure compounds, which may also incorporate uncatalyzed and homogeneously catalysed steps. Methods applying achiral heterogeneous catalysts in combination with soluble chiral chemical catalysts or biocatalysts are also presented. Sophisticated, finely tuned materials have been applied in most of these reactions, which have been discussed along with the main requirements necessary to perform these transformations in a one-pot manner.

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A chiral metal–organic framework for sequential asymmetric catalysis

Abstract: A chiral metal-organic framework (MOF) of the lcy topology was constructed from the Mn-Salen derived dicarboxylic acid and the [Zn(4)(μ(4)-O)(O(2)CR)(6)] secondary building unit, and used in highly regio- and stereo-selective sequential alkene epoxidation/epoxide ring-opening reactions.

Cited by 176 publications

References 37 publications

Metal-Organic Frameworks as Selective or Chiral Oxidation Catalysts

Metal-Organic Frameworks as Selective or Chiral Oxidation Catalysts

Chiral porous metal-organic frameworks with dual active sites for sequential asymmetric catalysis

Asymmetric one-pot reactions using heterogeneous chemical catalysis: recent steps towards sustainable processes

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