Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 12, Pages 7642-7651Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b00441
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Funding
- National Natural Science Foundation of China [21602129]
- Natural Science Basic Research Plan in Shaanxi Province of China [2017JM2020, 2017JM2001]
- Fundamental Research Funds for Central Universities [GK201803027]
- 111 Project [B14041]
- One Hundred Talented People of Shaanxi Province
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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 C-13 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.
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