ORGN 145 |
Ru(III)-catalyzed cyclization of arene-alkene substrates via intramolecular electrophilic hydroarylation
| So Won Youn, Department of Chemistry, Pukyong National University, Busan, 608-737, South Korea and Dalibor Sames, Department of Chemistry, Columbia University, 3000 Broadway, New York, NY 10027. |
| We report that RuCl3/AgOTf has proven to be an intramolecular hydroarylation catalyst of arene-ene substrates with an efficiency and scope superior to previously known methods. A variety of annulated arene heterocycles and carbocycles are accessible under mild conditions using this method in good to excellent yields, including chromane, tetralin, terpenoid, dihydrocoumarin, tetrahydroquinoline, and indolocyclohexane and cyclopentane systems. It is likely that this reaction proceeds via an electrophilic pathway involving alkene activation, C-C bond formation, and the protonation of a C-Ru intermediate. The contrast between the reactivity of arene-yne and arene-ene substrates raises interesting questions regarding the role of the metal catalyst on these seemingly related pathways. 
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Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Materials, Molecular Recognition
8:00 PM-10:00 PM, Sunday, August 22, 2004 Pennsylvania Convention Center -- Hall D, Poster
Division of Organic Chemistry
The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004
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