Transition-Metal-Free N–O Reduction of Oximes: A Modular Synthesis of Fluorinated Pyridines

An NH4I-based reductive system has been explored to promote the oxime N–O bond cleavage and thereby enable a modular synthesis of a broad range of pharmacologically significant fluorinated pyridines. Compared with traditional condensation methods for pyridine assembly, this protocol was found to be...

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Bibliographic Details
Published in:Organic letters 2017-07, Vol.19 (14), p.3743-3746
Main Authors: Huang, Huawen, Cai, Jinhui, Xie, Hao, Tan, Jing, Li, Feifei, Deng, Guo-Jun
Format: Article
Language:English
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Summary:An NH4I-based reductive system has been explored to promote the oxime N–O bond cleavage and thereby enable a modular synthesis of a broad range of pharmacologically significant fluorinated pyridines. Compared with traditional condensation methods for pyridine assembly, this protocol was found to be highly regio- and chemoselective and presented broad functional group tolerance.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b01564