title: Palladium(II)-catalyzed cyclizative cross-coupling of ortho-alkynylanilines with ortho-alkynylbenzamides under aerobic conditions.
abstract: 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.
authors.affiliation: Laboratory of Synthesis and Natural Product, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015 Lausanne (Switzerland) http://lspn.epfl.ch.
authors.forename: Bo
authors.initials: B
authors.lastname: Yao
authors.forename: Qian
authors.initials: Q
authors.lastname: Wang
authors.forename: Jieping
authors.initials: J
authors.lastname: Zhu
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000814:Aniline Compounds / Q000737:chemistry*; D001549:Benzamides / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D000814:Aniline Compounds; D001549:Benzamides; D010165:Palladium
keywords: cross-coupling; cyclization; heterocycles; palladium; synthetic methods