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Synfacts 2005(2): 0211-0211  
DOI: 10.1055/s-2005-916067
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

(Z)-β-Arylation of 2-Alkenylpyridines by C-H Activation Process

Contributor(s): V. Snieckus, Oleg M. Demchuk
S. Oi*, K. Sakai, Y. Inoue*
Tohoku University, Sendai, Japan
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Publikationsdatum:
25. Oktober 2005 (online)

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Significance

The direct β-arylation of 2-alkenylpyridines with aryl bromides using a ruthenium(II)-phosphine complex is reported. The reaction is quite general (12 examples) for a variety of alkenylpyridines and aryl bromides, proceeds in good to excellent yields, and, significantly, shows stereoselectivity opposite to the traditional Mizoroki-Heck reaction, which may be rationalized by a N-Ru coordinated intermediate derived in the initial C-H activation step.