Efficient Palladium-Catalyzed Nucleophilic Addition of Triorganoindium Reagents to Carbocyclic Derivatives

Palladium (0)-catalyzed allylic substitution reactions employing triorganoindium reagents have been investigated. In situ generated vinyl- and arylindiums react with substituted and unsubstituted cyclohex-2-enyl esters in the presence of 1−3 mol % Pd₂(dba)₃ to produce vinyl- or arylcyclohexenes in moderate to excellent yields. The stereoselectivity of this process was also examined, and evidence is presented that the reaction proceeds with inversion of stereochemical configuration.