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“On Water” Catalytic Aldol Reaction between Isatins and Acetophenones: Interfacial Hydrogen Bonding and Enamine Mechanism

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journal contribution
posted on 22.05.2019, 00:00 by Jinsong Han, Jin-Lei Zhang, Wei-Qiang Zhang, Ziwei Gao, Li-Wen Xu, Yajun Jian
“On water” catalytic aldol reaction catalyzed by polyetheramine (D230) has been developed for easy access to 3-substituted 3-hydroxyindolin-2-ones through the reaction between various substituted isatins and acetophenones/cyclic ketones in high yields under room temperature. Systematic mechanism investigation uncovers the secret for the on water catalytic aldol reaction: comparison of the heterogeneous and homogeneous reaction circumstances with yields of 95 and 20%, respectively, indicates the on-water reaction dominating; interfacial hydrogen bonding between isatin with H2O is tested based on the downfield shift of the C2 and C3’s 13C NMR signals when water was added to the CDCl3 solution of isatin; Lewis base polyetheramine D230 catalyzes the aldol reaction via the enamine mechanism verified by in situ NMR and ESI-MS analysis.