Chemoselectivity in Palladium-Catalyzed Reactions of 2-Bromoallyl Esters

Article abstract of DOI:10.1021/jo00220a043

The chemoselectivity of palladium-catalyzed reactions of 2-bromoallyl esters has been established.With compatible carbon nucleophiles, 2-bromoallyl esters gave products of couplling to the vinyl bromide moiety instead of nucleophilic allylic substitution.Products from reactions with nitrogen nucleophiles and in the absence of added nucleophiles are also consistent with the absence or minor importance of the (?-allyl)palladium complex formation as a competing pathway.These results illustrate an unusual influence of the 2-bromo substituent on the usual ease of fission of the allylic C-O bond.