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Title

MIL-101(Fe) as an active heterogeneous solid acid catalyst for the regioselective ring opening of epoxides by indoles

AuthorsNagarjun, Nagarathinam; Concepción, Patricia; Dhakshinamoorthy, Amarajothi
KeywordsIndole
Heterogeneous catalysis
Ring opening reaction
Metal organic frameworks
Solid acid
Issue DateFeb-2020
PublisherElsevier BV
CitationMolecular Catalysis
AbstractRingopeningofanepoxidebyanucleophileisconsideredasoneoftheviablestrategiestopreparebiologicallyactivemolecules using homogeneous or heterogeneous Lewis acid catalysts. Very often, the ring opening of epoxide wasperformed with oxygen, sulfur and nitrogen based nucleophiles. Recently, metal organic frameworks (MOFs) wereidentifiedasoneofthepromisingsolidheterogeneouscatalystsforringopeningofepoxidewithoxygenandnitrogenbasednucleophiles,buthowever,useofcarbonnucleophilelikeindoleislimited.Hence,thepresentworkreportsthecatalytic performance of MIL-101(Fe) as a highly active regioselective heterogeneous solid Lewis acid catalyst inpromoting the ring opening of styrene oxide by indole. Among the various catalysts employed for this reaction, MIL-101(Fe) exhibited the highest catalytic activity. A series of control experiments indicated the pivotal role played byLewisacidswithintheframeworksofMIL-101(Fe)andfurther,thecatalyticreactionwasfoundtobeheterogeneousinnature as evidenced by leaching test. Further, MIL-101(Fe) was reused four cycles with no decay in its activity. Also,MIL-101(Fe)exhibitedwidesubstratescopeinprovidingseriesofheterocycliccompoundsinmoderatetohigheryields.A suitable mechanism was also proposed considering the present results and the knowledge from the literature.
Publisher version (URL)https://www.sciencedirect.com/science/article/pii/S246882311930478X
URIhttp://hdl.handle.net/10261/220655
DOI10.1016/j.mcat.2019.110628
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