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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)


Abstract

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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Key Words

Hydroboration, Alkyl Amines


ID: J48-Y2012-1210