Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 361, Issue 9, Pages 2107-2116Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201801673
Keywords
Carbocatalyst; Graphene oxide; Metal-free conditions; Transamidation; Recyclability
Categories
Funding
- Uniersity Grants commission-UGC-CA
- Green Technology
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An environmentally friendly, inexpensive, carbocatalyst, graphene oxide (GO) promoted efficient, metal-free transamidation of various carboxamides with aliphatic, cyclic, and aromatic amines is demonstrated. The protocol is equally applicable to phthalimide, urea, and thioamide determining its adaptability. The oxygenated functionalities such as carbonyl (C=O), epoxy (O), carboxyl (COOH) and hydroxyl (OH), present on graphene oxide surface impart acidic properties to the catalyst. The graphene oxide being heterogeneous in nature, work efficiently under solvent-free reaction conditions providing desired products in good to excellent yields. The one-pot synthesis of 2,3-Dihydro-5H-benzo[b]-1,4-thiazepin-4-one moiety by GO catalyzed Aza Michael addition followed by intramolecular transamidation is also described. A plausible reaction mechanistic pathway involving H-bonding is discussed. The graphene oxide can be recycled and reused up to five cycles without much loss in catalytic activity.
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