The role of 4-(3-phenylpropyl)pyridine N-Oxide (P3NO) in the manganese-salen-catalyzed asymmetric epoxidation of indene

Senanayake, Chris H.; Smith, George B.; Ryan, Kenneth M.; Fredenburgh, Laura E.; Liu, Ji; Roberts, F. E.; Hughes, David L.; Larsen, Robert D.; Verhoeven, Thomas R.; Reider, Paul J.

doi:10.1016/0040-4039(96)00565-5

Cited by 71 publications

(24 citation statements)

References 6 publications

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“…42,53 In addition, various reports indicate that the use of donor ligands (substituted pyridine-N-oxides) slightly enhance the stability of the Mn-salen catalyst during the epoxidation reaction. 42,48,54,55 Presently, no mechanistic details for this degradation or the basis for the use of a stabilizing ligand have been reported. Our presented observations regarding the lack of stability for the homogeneous ligand, as well as its heterogeneous analogue, during exposure to NaOCl provide additional information as to the processes occurring in solution during epoxidation (beyond the commonly cited dimerization process 39 ) that prevent significant recovery and reuse of the homogeneous catalyst.…”

mentioning

confidence: 98%

Polymer-supported salen complexes for heterogeneous asymmetric synthesis: Stability and selectivity

Angelino¹,

Laibinis²

1999

J. Polym. Sci. A Polym. Chem.

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confidence: 98%

Polymer-supported salen complexes for heterogeneous asymmetric synthesis: Stability and selectivity

Angelino¹,

Laibinis²

1999

J. Polym. Sci. A Polym. Chem.

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“…Many research groups have reported that the presence of axial ligands, such as PPNO, [36] 4-phenylpropyl pyridine N-oxide, [37] and methylmorpholine-N-oxide, [38] in the Mn(salen) complexcatalyzed alkene epoxidation system can significantly improve the catalytic activity and selectivity of the Mn(salen) complex. The contribution of PPNO to the mono-or dimeric Mn(salen) complex-catalyzed alkene epoxidation reaction was studied, and the results are summarized in Table S1.…”

Section: Influence Of Axial Ligandmentioning

confidence: 99%

Epoxidation of Alkenes Catalyzed by Phenyl Group‐Modified, Periodic Mesoporous Organosilica‐Entrapped, Dimeric Manganese–Salen Complexes

et al. 2011

ChemSusChem

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A series of reusable, recoverable, diamine-bridged dimeric manganese-salen complexes were prepared by the encapsulation of homogeneous dimeric Mn(salen) complexes into nanocages of a 3D periodic mesoporous organosilica (PMO) support followed by silylation of the support with organosilane. The composition, structure, morphology, and textural properties of the prepared PMO-entrapped dimeric Mn(salen) complexes were characterized, and their catalytic performances were tested in the epoxidation of alkenes (styrene, cyclohexene, and 1-phenylcyclohexene), with NaClO as an oxygen source and 4-phenylpyridine-N-oxide as an axial ligand. Furthermore, the influences of the textural and morphological properties of the entrapped dimeric Mn(salen) complexes and the key reaction parameters on the catalytic activity and selectivity are discussed. Finally, the reusability of the supported dimeric Mn(salen) complexes was evaluated over three catalytic runs.

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Section: Introductionmentioning

confidence: 99%

“…Since the transportation of HOCl from water to oil phase is required for salen Mn(III) complexes catalyzed epoxidation, the design of the water soluble salen Mn(III) complexes become an attractive target. 27 To enhance the solubility of dimeric salen Mn(III) complexes in water, we used N,N-dibutylamine to substitute other groups of salicylaldehyde at the 5,5 0 positions. 28,29 Herein, we have extended the application of chiral dimeric salen Mn(III) complexes in the asymmetric epoxidation using NaOCl as an terminal oxidant with various reaction solvents.…”

Section: Introductionmentioning

confidence: 99%

Asymmetric epoxidation of olefins using novel chiral dinuclear Mn(III)‐Salen complexes with inherent phase‐transfer capability in ionic liquids

et al. 2010

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Two new chiral dinuclear Mn(III)-Salen complexes with inherent phase-transfer capability have been synthesized, which serve as catalysts in the asymmetric epoxidation of nonfunctionalized alkenes. Experimental results show these complexes are effective catalysts for the asymmetric epoxidation of some cyclic alkenes and the catalysts have certain inherent phase-transfer capability during the epoxidation because of their weak water solubility. In general, good enantioselectivity and acceptable yields were achieved when NaClO was used as oxidant under three different reaction systems. Among these alkenes, the catalyst 6a gave the highest ee (94%) for 6-chloro-2,2-dimethylchromene in the presence of ionic liquid 2. Additionally, the recovery and recycling of one dimeric Mn(III)-Salen complex were tested to investigate atom efficiency of the catalyst in different reaction systems on the alkenes epoxidations. The catalyst 6a could be recovered and recycled for six times without losing activity and selectivity.

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The role of 4-(3-phenylpropyl)pyridine N-Oxide (P3NO) in the manganese-salen-catalyzed asymmetric epoxidation of indene

Cited by 71 publications

References 6 publications

Polymer-supported salen complexes for heterogeneous asymmetric synthesis: Stability and selectivity

Polymer-supported salen complexes for heterogeneous asymmetric synthesis: Stability and selectivity

Epoxidation of Alkenes Catalyzed by Phenyl Group‐Modified, Periodic Mesoporous Organosilica‐Entrapped, Dimeric Manganese–Salen Complexes

Asymmetric epoxidation of olefins using novel chiral dinuclear Mn(III)‐Salen complexes with inherent phase‐transfer capability in ionic liquids

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