A Simple, Modular Synthesis of Substituted Pyridines
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- 9 May 2008
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 130 (22), 6918-6919
- https://doi.org/10.1021/ja8013743
Abstract
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 α,β-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.Keywords
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