title: Synthesis of tertiary alkyl amines from terminal alkenes: copper-catalyzed amination of alkyl boranes.
abstract: A method for highly selective anti-Markovnikov hydroamination of terminal alkenes is reported. The one-pot procedure involves hydroboration of the alkene followed by a novel electrophilic amination of the alkyl borane catalyzed by an NHC-Cu complex. Terminal alkenes are successfully transformed into tertiary alkyl amines in the presence of a variety of functional groups in yields ranging from 80 to 97% with excellent regioselectivity. Results of a preliminary study of the reaction mechanism are also described.
authors.affiliation: Department of Chemistry, University of Washington, Seattle, Washington 98195, USA.
authors.forename: Richard P
authors.initials: RP
authors.lastname: Rucker
authors.forename: Aaron M
authors.initials: AM
authors.lastname: Whittaker
authors.forename: Hester
authors.initials: H
authors.lastname: Dang
authors.forename: Gojko
authors.initials: G
authors.lastname: Lalic
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000588:Amines / Q000138:chemical synthesis*; D001880:Boranes / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*
chemical_list: D000475:Alkenes; D000588:Amines; D001880:Boranes; D003300:Copper