Auxiliary-directed etherification of sp 2 C-H bonds under heterogeneous metal-organic framework catalysis: synthesis of ethenzamide

An efficient protocol for 8-aminoquinoline assisted alkoxylation and phenoxylation of sp C-H bonds under heterogeneous catalysis was developed. The optimal conditions employed Cu-MOF-74 (20%), K CO base, pyridine ligand or dimethyl formamide solvent, and O oxidant at 80 °C or 100 °C for 24 hours. Cu...

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Bibliographic Details
Published in:RSC advances 2018-01, Vol.8 (5), p.2829-2836
Main Authors: Tran, Chau B, Duong, Xuan N T, Lu, Huy D, Cao, Thu T V, Truong, Thanh
Format: Article
Language:English
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Summary:An efficient protocol for 8-aminoquinoline assisted alkoxylation and phenoxylation of sp C-H bonds under heterogeneous catalysis was developed. The optimal conditions employed Cu-MOF-74 (20%), K CO base, pyridine ligand or dimethyl formamide solvent, and O oxidant at 80 °C or 100 °C for 24 hours. Cu-MOF-74 revealed remarkably higher activity when compared with other previously commonly used Cu-MOFs in cross coupling reactions, supported copper catalysts, and homogeneous copper salts. The reaction scope with respect to coupling partners included a wide range of various substrates. Interestingly, the developed conditions are applicable for the synthesis of high-profile relevant biological agents from easily accessible starting materials. Furthermore, a leaching test confirmed the reaction heterogeneity and the catalyst was reused and recycled at least 8 times with trivial degradation in activity.
ISSN:2046-2069
2046-2069
DOI:10.1039/C7RA12010A