Metal-Free Assembly of Polysubstituted Pyridines from Oximes and Acroleins

The Journal of Organic Chemistry
Huawen HuangGuo-Jun Deng

Abstract

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.

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May 24, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·John C Walton
Feb 6, 2017·Organic & Biomolecular Chemistry·Hai-Bin Yang, Nicklas Selander
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Mar 23, 2019·The Journal of Organic Chemistry·Raghuram GujjarappaChandi C Malakar
Dec 10, 2016·The Journal of Organic Chemistry·Yajie FuBaohua Chen

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