Synthesis of Tertiary Alkyl Amines from Terminal Alkenes: Copper-Catalyzed Amination of Alkyl Boranes

摘要

A method for highly selective anti-Markov-nikov 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 regiose-lectivity. Results of a preliminary study of the reaction mechanism are also described.