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![Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F51444.jpg&w=3840&q=50)
Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
Published on: March 20, 2014
Ligand Development Enabled Cu-Catalyzed Coupling of (Hetero)aryl Chlorides and Ammonia with Higher Turnovers
Siqi Wang1, Kaiyuan Cheng1, Dawei Ma2
1Chang-Kung Chuang Institute, School of Chemistry and Molecular Engineering, East China Normal University, 500 Dongchuan Lu, Shanghai200062, China.
Abstract:
An oxalohydrazide derived from 2,7-di-tert-butylcarbazole was identified as a highly effective ligand in the copper-catalyzed coupling of (hetero)aryl chlorides with aqueous ammonia. This system enables the reaction to proceed smoothly with a catalyst loading as low as 0.1 mol % at 120 °C─the lowest loading ever reported for such metal-catalyzed transformations. The same catalytic system also allows coupling of (hetero)aryl chlorides at 80 °C and (hetero)aryl bromides at room temperature, each representing the lowest temperatures yet achieved for these coupling reactions.
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