Computational study on the catalyst-controlled synthesis of C2-substituted quinolines through the annulation of 2-vinylanilines and alkynoates

Publication date: Available online 20 June 2019Source: Journal of Organometallic ChemistryAuthor(s): Jing Zhang, Jing-Ning Lv, Fengyue Zhao, Jiaying SunAbstractDensity functional theory (DFT) calculations were employed to study the reaction mechanisms of the synthesis of C-2 functionalized indole/quinoline catalyzed by TfOH/Pd(OAc)2. Our calculated results verify the experimental phenomena that the selectivity for this reaction is catalyst-controlled. The product is C-2 functionalized indole by employing the sole catalyst TfOH. While the product will become 4-phenylquinoline-2-carboxylate by adding another catalyst TfOH. The electronic effects contribute to the selectivity.

Source: Journal of Organometallic Chemistry - June 20, 2019 Category: Chemistry Source Type: research