title: Direct benzylic metalation of a phenethylamine derivative: potassium as the key to both generation and stabilization of a labile anion.
abstract: t-BuLi-t-BuOK selectively metalates the benzylic position of 2-phenylethyldimethylamine under mild conditions without occurrence of β-elimination in the resulting metalated species. Theoretical and structural studies indicate that potassium is crucial for both the lowering of the barrier of the initial deprotonation step and the stabilization of the labile anion.
authors.affiliation: Anorganische Chemie, Technische Universität Dortmund, Otto-Hahn-Strasse 6, D-44227 Dortmund, Germany.
authors.forename: Christian
authors.initials: C
authors.lastname: Unkelbach
authors.forename: Hannah S
authors.initials: HS
authors.lastname: Rosenbaum
authors.forename: Carsten
authors.initials: C
authors.lastname: Strohmann
mesh_terms: D000838:Anions / Q000737:chemistry; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry; D010627:Phenethylamines / Q000737:chemistry*; D011188:Potassium / Q000737:chemistry*
chemical_list: D000838:Anions; D009942:Organometallic Compounds; D010627:Phenethylamines; C046771:butyllithium; C029261:phenethylamine; D011188:Potassium