Palladium(II)-catalyzed cyclizative cross-coupling of ortho-alkynylanilines with ortho-alkynylbenzamides under aerobic conditions

Article abstract of DOI:10.1002/anie.201307738

Born to couple: The Pd(OAc)₂-catalyzed reaction of o-alkynylanilines (1) with o-alkynylbenzamides (2) affords the cyclizative cross-coupling products 3 in good to excellent yields. Three bonds are created in the formation of two heterocycles tethered by a tetrasubstituted double bond. Mechanistic studies indicate that the reaction is initiated by aminopalladation with subsequent oxypalladation, N-demethylation, and reductive elimination. Copyright