om5b00581_si_002.cif (227.71 kB)

Palladium-Catalyzed Selective β‑Arylation of Aliphatic Amides Using a Removable N,O‑Bidentate Auxiliary

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posted on 14.09.2015, 00:00 by Shou-Kun Zhang, Xin-Yan Yang, Xue-Mei Zhao, Peng-Xiang Li, Jun-Long Niu, Mao-Ping Song
A new method for palladium-catalyzed β-arylation of aliphatic and cycloaliphatic amides without conventional silver salts utilizing 2-aminopyridine-1-oxide moiety (PyO) as an N,O-bidentate group has been developed. Reactions proceeded smoothly in DMSO solvent in the presence of K2HPO4·3H2O, providing the β-arylated aliphatic amide products in a moderate-to-good yield. An important cyclopalladium intermediate, successfully obtained with a modest yield, could be converted to the monoarylation product and be used as catalyst in arylation reaction. Moreover, the PyO directing group was easily removed under base condition to generate aliphatic acids.