A tandem catalytic approach to methyleneindenes: mechanistic insights into gem-dibromoolefin reactivity.
The methylenindene scaffold can be prepared from readily available gem-dibromoolefins using an efficient palladium-catalyzed tandem intermolecular Suzuki/intramolecular Heck reaction. The reaction is highly modular and proceeds 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.
Bryan
Christopher S
CS
Davenport Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario, Canada M5S 3H6.
Lautens
Mark
M
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D007192:Indenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*
D000475:Alkenes; D006842:Hydrocarbons, Brominated; D007192:Indenes; D010165:Palladium