Synthesis and Chemistry of Alkylpalladium Compounds Prepared via Vinylpalladation of Bicyclic Alkenes

Article abstract of DOI:10.1021/jo00363a009

Vinylmercuric chlorides, Li2PdCl4, and bicyclic alkenes react to form stable, isolable adducts (1-9) in which the vinyl and PdCl groups have been added in a cis, exo fashion across the carbon-carbon double bond.Norbornadiene under the same conditions affords an endo nortricyclyl adduct 10.These compounds have been fully characterized and undergo reactions with CO-CH3OH-Et3N, NaBH4, NaOCH3-CH3OH, H2, RLi, CuCN, and Pb(OAc)4 to give methyl esters, reduced alkanes and alkenes, cross-coupled hydrocarbons, nitriles, and acetates.