Abstract
Porous chitosan microspheres-supported palladium catalysed the amination of aryl halides with a wide variety of secondary amines to yield the corresponding cross-coupling products under aerobic conditions. Both aryl bromides and iodides gave good to excellent yields of N,N-disubstituted anilines. The procedure can tolerate common functional groups such as chloro, methoxyl and nitro. The heterogeneous catalysis is efficienct and the catalyst could be recycled seven times without obvious decreased conversion.
Keywords
References
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