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...

Full description

Saved in:
Bibliographic Details
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
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201900751