Ortho Vinylation of Aromatic Amides via Cyclopalladation Complexes

Article abstract of DOI:10.1021/jo00335a019

The reaction of acetanilide and meta- and para-substituted acetanilides with palladium acetate has given new ortho-palladated complexes 2a-j, which reacted with carbon monoxide, ethylene, or methyl vinyl ketone to produce the corresponding N-acylanthranilic esters 4a-m, 2-acetaminostyrenes 9k-p, and 4-aryl-3-buten-2-one derivatives 9a-j, respectively.Reactions of 2a with substituted olefins proceeded readily to give the 2-<(acetylamino)phenyl>olefins 8a-h.Ortho-substituted acetanilides and N-methylacetanilide did not undergo complex formation with palladium acetate.