Palladium(II)-Promoted Cross-Coupling of 4-Alkenyl-2-azetidinones with Organomercurials

Article abstract of DOI:10.1021/jo00060a024

The palladium-promoted cross-coupling of 4-alkenyl-2-azetidinones with aryl and vinylic mercurials provides 5-aryl-3-alkenamides and 3,6-alkadienamides, respectively.Modest to excellent stereoselectivity for formation of the new carbon-carbon double bond is observed.The reaction becomes catalytic in palladium when cupric chloride and oxygen are introduced.This process constituted the first organometallic ring opening of 2-azetidinones to acyclic unsaturated amides.