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Synfacts 2008(9): 0919-0919  
DOI: 10.1055/s-2008-1078616
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 2-Arylpyridines via Stille Coupling-Azaelectrocyclization

Contributor(s): Victor Snieckus, Jignesh J. Patel
T. Kobayashi, S. Hatano, H. Tsuchikawa, S. Katsumura*
Kwansei Gakuin University, Hyogo, Japan
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Publication History

Publication Date:
22 August 2008 (online)

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Significance

A one-pot synthesis of 2-arylpyr­idines D is achieved by reaction of vinylstannes A, iodoolefin B, and methanesulfonamide C under Pd catalysis. The reaction is suggested to proceed via a Stille coupling followed by formation of an azatriene which undergoes 6p-electrocyclization and aromatization by base-catalyzed elimination to form product D.