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MIL-101(Fe) as an active heterogeneous solid acid catalyst for the regioselective ring opening of epoxides by indoles
Molecular Catalysis ( IF 4.6 ) Pub Date : 2019-11-27 , DOI: 10.1016/j.mcat.2019.110628
Nagarathinam Nagarjun , Patricia Concepcion , Amarajothi Dhakshinamoorthy

Ring opening of an epoxide by a nucleophile is considered as one of the viable strategies to prepare biologically active molecules using homogeneous or heterogeneous Lewis acid catalysts. Very often, the ring opening of epoxide was performed with oxygen, sulfur and nitrogen based nucleophiles. Recently, metal organic frameworks (MOFs) were identified as one of the promising solid heterogeneous catalysts for ring opening of epoxide with oxygen and nitrogen based nucleophiles, but however, use of carbon nucleophile like indole is limited. Hence, the present work reports the catalytic performance of MIL-101(Fe) as a highly active regioselective heterogeneous solid Lewis acid catalyst in promoting 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 by Lewis acids within the frameworks of MIL-101(Fe) and further, the catalytic reaction was found to be heterogeneous in nature as evidenced by leaching test. Further, MIL-101(Fe) was reused four cycles with no decay in its activity. Also, MIL-101(Fe) exhibited wide substrate scope in providing series of heterocyclic compounds in moderate to higher yields. A suitable mechanism was also proposed considering the present results and the knowledge from the literature.



中文翻译:

MIL-101(Fe)作为活性非均相固体酸催化剂,用于吲哚对环氧化物的区域选择性开环

亲核试剂对环氧化物的开环被认为是使用均相或非均相路易斯酸催化剂制备生物活性分子的可行策略之一。通常,环氧化物的开环是基于氧,硫和氮的亲核试剂进行的。最近,金属有机骨架(MOF)被确定为有前途的固态多相催化剂之一,可用于环氧基与氧和氮基亲核试剂的开环,但是碳亲核试剂如吲哚的使用受到限制。因此,本工作报道了MIL-101(Fe)作为高活性区域选择性多相固体路易斯酸催化剂的催化性能,其通过吲哚促进了苯乙烯氧化物的开环。在用于该反应的各种催化剂中,MIL-101(Fe)表现出最高的催化活性。一系列对照实验表明,路易斯酸在MIL-101(Fe)的骨架中发挥了关键作用,此外,通过浸出试验证明,催化反应本质上是异质的。此外,MIL-101(Fe)被重复使用了四个周期而活性没有下降。同样,MIL-101(Fe)在以中等到更高的产率提供一系列杂环化合物方面表现出了广泛的底物范围。考虑到目前的结果和来自文献的知识,还提出了一种合适的机制。MIL-101(Fe)在以中等到较高的产率提供一系列杂环化合物方面表现出广泛的底物范围。考虑到目前的结果和来自文献的知识,还提出了一种合适的机制。MIL-101(Fe)在以中等到较高的产率提供一系列杂环化合物方面表现出广泛的底物范围。考虑到目前的结果和来自文献的知识,还提出了一种合适的机制。

更新日期:2019-11-28
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