title: Umpolung Synthesis of Diarylmethylamines via Palladium-Catalyzed Arylation ofN-Benzyl Aldimines.
abstract: An umpolung synthesis of diarylmethylamine derivatives is presented. This reaction entails a Pd catalyzed arylation of 1,3-diaryl-2-azaallyl anions,in situgenerated fromN-benzyl aldimines. A Pd(NIXANTPHOS)-based catalyst together with hindered silylamide bases enabled the coupling of aldimines with aryl bromides in good to excellent yields without product isomerization. Moreover, regioselectivity in the arylation of unsymmetrical 1,3-diaryl-2-azaallyl anions was studied. This method is suitable for a gram scale synthesis of diarylmethylamine derivatives at room temperature without use of a glovebox.
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
authors.forename: Minyan
authors.initials: M
authors.lastname: Li
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.|Istanbul Technical University, Science Faculty, Department of Chemistry, Maslak 34469, Istanbul, Turkey.
authors.forename: Baris
authors.initials: B
authors.lastname: Yucel
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.|Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, Av. San Claudio y 14 Sur, Puebla, Pue 72570, México.
authors.forename: Jacqueline
authors.initials: J
authors.lastname: Jiménez
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
authors.forename: Madeline
authors.initials: M
authors.lastname: Rotella
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
authors.forename: Yue
authors.initials: Y
authors.lastname: Fu
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: Walsh
keywords: 2-azaallyl anion; NIXANTPHOS; diarylmethylamines; regioselectivity; umpolung