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

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• 作者：Shou-Kun Zhang ; Xin-Yan Yang ; Xue-Mei Zhao ; Peng-Xiang Li ; Jun-Long Niu ; Mao-Ping Song
• 刊名：Organometallics
• 出版年：2015
• 出版时间：September 14, 2015
• 年：2015
• 卷：34
• 期：17
• 页码：4331-4339
• 全文大小：497K
• ISSN：1520-6041

文摘

A new method for palladium-catalyzed 尾-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路3H₂O, providing the 尾-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.