A Tandem Catalytic Approach to Methyleneindenes: Mechanistic Insights into gem-Dibromoolefin Reactivity
Christopher S. Bryan and Mark Lautens*
*Davenport Laboratories, Department of Chemistry, University
of Toronto, Toronto, Ontario, Canada M5S 3H6, Email: mlautens
chem.utoronto.ca
C. S. Bryan, M. Lautens, Org. Lett., 2010, 12, 2754-2757.
DOI: 10.1021/ol100844v
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Abstract
The methylenindene scaffold can be prepared from readily available gem-dibromoolefins using an efficient, highly modular palladium-catalyzed tandem intermolecular Suzuki/intramolecular Heck reaction under mild conditions. The choice of ligand was found to be crucial to control the selectivity of the reaction. Isolation of intermediates under different conditions provides insight into the mechanism.
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Key Words
Indenes, Suzuki Coupling, Heck Reaction
ID: J54-Y2010-1660
