Synthesis of tertiary alkyl amines from terminal alkenes: copper-catalyzed amination of alkyl boranes

Richard P Rucker; Aaron M Whittaker; Hester Dang; Gojko Lalic

doi:10.1021/ja3023829

Synthesis of tertiary alkyl amines from terminal alkenes: copper-catalyzed amination of alkyl boranes

J Am Chem Soc. 2012 Apr 18;134(15):6571-4. doi: 10.1021/ja3023829. Epub 2012 Apr 10.

Authors

Richard P Rucker¹, Aaron M Whittaker, Hester Dang, Gojko Lalic

Affiliation

¹ Department of Chemistry, University of Washington, Seattle, Washington 98195, USA.

PMID: 22469028
DOI: 10.1021/ja3023829

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.

MeSH terms

Alkenes / chemistry*
Amines / chemical synthesis*
Boranes / chemistry*
Catalysis
Copper / chemistry*

Substances

Alkenes
Amines
Boranes
Copper