Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 130, Issue 22, Pages 6918-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja8013743
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Funding
- NIGMS NIH HHS [R01 GM066153-22, GM066153, R01 GM066153-22S1, R01 GM066153, R01 GM066153-21] Funding Source: Medline
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A simple, modular method to prepare highly substituted pyridines is disclosed. The method employs a cascade reaction comprising (1) a novel N-iminative, Cu-catalyzed cross-coupling of alkenylboronic acids at the N-O bond of alpha,beta-unsaturated ketoxime O-pentafluorobenzoates, (2) electrocyclization of the resulting 3-azatriene, and (3) air oxidation affording highly substituted pyridines in moderate to excellent isolated yields (43-91%). Starting materials are readily available, and functional group tolerance is very good.
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