Metal-Free Assembly of Polysubstituted Pyridines from Oximes and Acroleins

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...

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Bibliographic Details
Published in:Journal of organic chemistry 2016-02, Vol.81 (4), p.1499-1505
Main Authors: Huang, Huawen, Cai, Jinhui, Tang, Lichang, Wang, Zilong, Li, Feifei, Deng, Guo-Jun
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b02624