1379454-75-7Relevant academic research and scientific papers
An efficient synthesis of N-substituted indoles from indoline/indoline carboxylic acid via aromatization followed by C-N cross-coupling reaction by using nano copper oxide as a recyclable catalyst
Reddy, K. Harsha Vardhan,Satish,Ramesh,Karnakar,Nageswar
, p. 3061 - 3065 (2012)
A new and elegant protocol for the synthesis of 1-substituted indoles was developed via aromatization of indoline/indoline carboxylic acid followed by C-N cross-coupling with various aryl halides in the presence of nano CuO as a recyclable catalyst, Cs2CO3 as a base in DMSO at 80 °C. 1-Substituted indoles were obtained in good to excellent yields and the catalytic system can be recycled up to four cycles without loss of catalytic activity.
Scope, Kinetics, and Mechanism of “On Water” Cu Catalysis in the C–N Cross-Coupling Reactions of Indole Derivatives
Malavade, Vrunda,Patil, Manish,Patil, Mahendra
supporting information, p. 561 - 569 (2020/02/05)
A simple and cost-effective protocol for the C–N cross coupling of indole derivatives with aryl iodides using CuI/phenanthroline catalytic system in aqueous and DME/H2O solvent mixture is described. The reactions were performed in the absence of phase-transfer catalyst, and afforded N-arylated products in moderate to excellent yields under mild reaction conditions. A systematic tuning of reaction conditions using DME as a co-solvent enables to improve product yields of N-arylation reactions. The broad substrate scope, easy performance, and low loading of catalyst as well as ligand render this approach appropriate for large scale processes. The mechanism of “on water” Cu-catalyzed N-arylation reaction is investigated using kinetic and computational studies, which reveal interesting mechanistic aspects of the reaction. A series of kinetic experiments showed significant rate enhancement for “on water” Cu-catalyzed N-arylation over the reaction performed in the organic solvent (DME). Computational studies corroborated “on water” rate acceleration by delineating the role of water in the reaction. The water induces rate acceleration by stabilizing the transition state of oxidative addition through hydrogen bonding interactions, presumably at the oil-water interface, and thus helps to reduce the free energy of activation of oxidative addition of iodobenzene to the Cu complex, which is identified as the rate-limiting step of reaction.
Green synthesis of predominant (1 1 1) facet CuO nanoparticles: Heterogeneous and recyclable catalyst for N-arylation of indoles
Suramwar, Nikhil V.,Thakare, Sanjay R.,Karade, Nandkishor N.,Khaty, Niren T.
experimental part, p. 28 - 34 (2012/07/14)
Well faceted CuO nanoparticles were synthesized by thermal-assisted green strategy at reflux temperature in a short period of time. A possible growth mechanism of such highly faceted nanostructures based on typical biomolecule-crystal interactions in aque
