Journal of Organic Chemistry 2003-11-28

Palladium charcoal-catalyzed Suzuki-Miyaura coupling to obtain arylpyridines and arylquinolines.

Tsuyoshi Tagata, Mayumi Nishida

文献索引：J. Org. Chem. 68(24) , 9412-5, (2003)

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摘要

A phosphine ligand, such as PPh3 or 2-(dicyclohexylphosphino)biphenyl, is essential for the Pd/C-catalyzed Suzuki-Miyaura coupling of halopyridines and haloquinolines, although it has been reported that the reaction of phenyl chlorides can be catalyzed by nonprereduced Pd/C without any additives. In the reactions of bromopyridines, bromoquinolines, 2-chloropyridines, and 2-chloroquinolines, PPh3 was effective enough to provide coupling products in good yields. However, in the reactions of 3-chloropyridine, 4-chloropyridine, and 6-chloroquinoline, sterically hindered 2-(dicyclohexylphosphino)biphenyl was indispensable as a ligand.