Metal-Free Assembly of Polysubstituted Pyridines from Oximes and Acroleins

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• 作者：Huawen Huang ; Jinhui Cai ; Lichang Tang ; Zilong Wang ; Feifei Li ; Guo-Jun Deng
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：February 19, 2016
• 年：2016
• 卷：81
• 期：4
• 页码：1499-1505
• 全文大小：435K
• ISSN：1520-6904

文摘

Transition-metal-catalyzed synthesis of N-heterocycles from oximes has been previously well established. In this paper, for the first time a metal-free protocol with the combinational employment of iodine and triethylamine has been demonstrated to be effective to trigger the oxime-based synthesis of pyridines with high chemo-selectivity and wide functional group tolerance. A broad range of functional pyridines were prepared in moderate to excellent yields. While neither iodine nor triethylamine could trigger this transformation, mechanistic experiments indicated a radical pathway for the reaction. The resultant 2-aryl-substituted pyridines have been proved to be versatile building blocks in a range of transition-metal-catalyzed C–H functionalization reactions.