title: Catalytic C-H activation of phenylethylamines or benzylamines and their annulation with allenes.
abstract: Tetrahydro-3-benzazepines and tetrahydroisoquinolines are synthesized in one step from allenes and phenylethylamines or benzylamines, respectively. Mechanistically, it is assumed that activation of a C-H bond of an aromatic ring with Pd(II) occurs, directed by the primary amine, leading to the formation of a palladacycle into which an allene then undergoes insertion. The resulting π-allyl intermediate cyclizes to the products by an intramolecular allylic alkylation. The process is particularly useful with 2,3-butadienoates and amines having a quaternary carbon at the α-position.
authors.affiliation: Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona , Martí i Franquès 1, 08028 Barcelona, Spain.
authors.forename: Aleix
authors.initials: A
authors.lastname: Rodríguez
authors.forename: Joan
authors.initials: J
authors.lastname: Albert
authors.forename: Xavier
authors.initials: X
authors.lastname: Ariza
authors.forename: Jordi
authors.initials: J
authors.lastname: Garcia
authors.forename: Jaume
authors.initials: J
authors.lastname: Granell
authors.forename: Jaume
authors.initials: J
authors.lastname: Farràs
authors.forename: Andrea
authors.initials: A
authors.lastname: La Mela
authors.forename: Ernesto
authors.initials: E
authors.lastname: Nicolás
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D000478:Alkylation; D001596:Benzylamines / Q000737:chemistry*; D002070:Butadienes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006860:Hydrogen Bonding; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D010627:Phenethylamines / Q000737:chemistry*
chemical_list: D000466:Alkadienes; D001596:Benzylamines; D002070:Butadienes; D010627:Phenethylamines; C025947:propadiene; D010165:Palladium