Unified and Benign Synthesis of Spirooxindoles via Bifunctional and Recyclable Iodide‐Salt‐Catalyzed Oxidative Coupling in Water

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, sp...

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Published in:European journal of organic chemistry 2019-09, Vol.2019 (35), p.6028-6033
Main Authors: Wang, Dangui, Lu, Xunbo, Sun, Shaohan, Yu, Huaibin, Su, Huimin, Wu, Yuzhou, Zhong, Fangrui
Format: Article
Language:English
Subjects:
Aqueous solutions
Carbonyls
Catalysis
Homogeneous catalysis
Hydrogen peroxide
Iodine
Micellar catalysis
Oxidative coupling
Oxygenation
Recyclability
Spirooxindoles
Substrates
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cited_by cdi_FETCH-LOGICAL-c3171-20976c79a94561152c4920b7e9417c63c2267e338752c571b8e8ad5af0c33aa33
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container_issue 35
container_start_page 6028
container_title European journal of organic chemistry
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creator Wang, Dangui
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description 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 H2O2 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. A micellar catalytic system based on amphiphilic bifunctional iodide salts is developed for oxidative α‐functionalization carbonyl substrates in water, enabling unified and benign synthesis of various 2‐oxindoles containing spirotetrahydrobenzofurans, spiroisochromanones, spiroindolines and spirolactones.
doi_str_mv 10.1002/ejoc.201900751
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subjects Aqueous solutions
Carbonyls
Catalysis
Homogeneous catalysis
Hydrogen peroxide
Iodine
Micellar catalysis
Oxidative coupling
Oxygenation
Recyclability
Spirooxindoles
Substrates
title Unified and Benign Synthesis of Spirooxindoles via Bifunctional and Recyclable Iodide‐Salt‐Catalyzed Oxidative Coupling in Water
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