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Synfacts 2006(2): 0115-0115  
DOI: 10.1055/s-2005-924822
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Azabiaryls by a non-Cross-Coupling Method

Contributor(s): V. Snieckus, Oleg M. Demchuk
E. J. Corey*, Y. Tian
Harvard University, Cambridge, USA
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Publication History

Publication Date:
23 January 2006 (online)

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Significance

An efficient C-4-selective arylation of pyridines by triflic anhydride activation is reported. The reaction undoubtedly is driven by the reactivity of the N-triflylpyridinium salt and leads to dihydropyridines, which are rearomatized to pyridines in excellent yields. The reaction of pyridines with TMSCN and allyl-SnBu3 to afford the corresponding 1,2- or 1,4-adducts albeit in low yields is also reported.