title: Rapid and efficient access to secondary arylmethylamines.
abstract: Ammoniomethyl trifluoroborates are very powerful reagents that can be used to access biologically relevant aryl- and heteroaryl-methylamine motifs via Suzuki-Miyaura cross-couplings. Until now, this method was limited to the production of tertiary and primary amines. The synthesis of a large array of secondary ammoniomethyltrifluoroborates has been achieved through a one step nucleophilic substitution reaction on the potassium bromomethyltrifluoroborate. Smooth cross-coupling conditions have been designed, based on the use of an aminobiphenyl palladium precatalyst, to couple these trifluoroborates efficiently with aryl bromides. This strategy offers a new way to access biologically relevant motifs and allows, with the previously developed methods, access to all three classes of aminomethylarenes.
authors: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323, USA.
authors: Nicolas
authors: N
authors: Fleury-Brégeot
authors: Jessica
authors: J
authors: Raushel
authors: Deidre L
authors: DL
authors: Sandrock
authors: Spencer D
authors: SD
authors: Dreher
authors: Gary A
authors: GA
authors: Molander
mesh_terms: D001881:Borates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D008744:Methylamines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry
chemical_list: D001881:Borates; D006845:Hydrocarbons, Fluorinated; D008744:Methylamines; D010165:Palladium; C027451:methylamine