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Unified and Benign Synthesis of Spirooxindoles via Bifunctional and Recyclable Iodide‐Salt‐Catalyzed Oxidative Coupling in Water
Author(s) -
Wang Dangui,
Lu Xunbo,
Sun Shaohan,
Yu Huaibin,
Su Huimin,
Wu Yuzhou,
Zhong Fangrui
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900751
Subject(s) - chemistry , amination , bifunctional , catalysis , iodide , oxidative coupling of methane , intramolecular force , amphiphile , aqueous solution , salt (chemistry) , combinatorial chemistry , aqueous medium , oxidative phosphorylation , organic chemistry , biochemistry , copolymer , polymer
Herein we develop a novel micellar catalytic system based on amphiphilic bifunctional iodide salts for oxidative intramolecular α‐oxygenation and α‐amination of carbonyl substrates in water, thus enabling a unified and benign synthesis of various 2‐oxindoles containing spirotetrahydrobenzofurans, spiroisochromanones, spiroindolines and spirolactones. Notably, the terminal oxidant H 2 O 2 produced water as the only by‐product. The excellent recyclability of the aqueous medium containing the catalyst further highlights the synthetic utility of this system.