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Metal-Free Assembly of Polysubstituted Pyridines from Oximes and Acroleins

Huawen Huang*, Jinhui Cai, Lichang Tang, Zilong Wang, Feifei Li and Guo-Jun Deng*

*Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, China, Email: hwhuangxtu.edu.cn, gjdengxtu.edu.cn

H. Huang, J. Cai, L. Tang, Z. Wang, F. Li, G.-J. Deng, J. Org. Chem., 2016, 81, 1499-1505.

DOI: 10.1021/acs.joc.5b02624 (free Supporting Information)


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Abstract

The combination of iodine and triethylamine triggers an oxime-based synthesis of 2-aryl-substituted pyridines with high chemo-selectivity and wide functional group tolerance. A broad range of functional pyridines were prepared in good yields using this metal-free protocol. While neither iodine nor triethylamine could trigger this transformation, mechanistic experiments indicated a radical pathway for the reaction.

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Key Words

pyridines


ID: J42-Y2016