Synthesis of Tertiary Alkyl Amines from Terminal Alkenes: Copper-Catalyzed Amination of Alkyl Boranes
Richard P. Rucker, Aaron M. Whittaker, Hester Dang and Gojko Lalic*
*Department of Chemistry, University of Washington, Seattle, Washington 98195, United States, Email: lalicchem.washington.edu
R. P. Rucker, A. M. Whittaker, H. Dang, G. Lalic, J. Am. Chem. Soc., 2012, 134, 6571-6574.
DOI: 10.1021/ja3023829 (free Supporting Information)
A method for highly selective anti-Markovnikov hydroamination of terminal alkenes 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 very good yields ranging with excellent regioselectivity.
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