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Copper(II)-Catalyzed CC Bond-Forming Reactions of α-Electron-Withdrawing Group-Substituted Ketene S,S-Acetals with Carbonyl Compounds and a Facile Synthesis of Coumarins

✍ Scribed by Hong-Juan Yuan; Mang Wang; Ying-Jie Liu; Qun Liu


Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
169 KB
Volume
351
Category
Article
ISSN
1615-4150

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✦ Synopsis


A new catalytic C À C bond-forming reaction has been developed. Catalyzed by cheap and commercially available copper(II) bromide (CuBr 2 ; 10 mol%), the reactions of a-electron-withdrawing group (EWG)-substituted ketene S,S-acetals with aldehydes or ketones in acetonitrile at room temperature gave a variety of densely functionalized coupling products in excellent yields (80-98%). Based on this catalytic process, coumarin derivatives were efficiently synthesized when salicylaldehydes were selected as the carbonyl components.