Synlett 2013; 24(3): 269-275
DOI: 10.1055/s-0032-1317744
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© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Electrophilic Amination of Organoboron Compounds

Gojko Lalic*
Department of Chemistry, University of Washington, Seattle, WA 98105, USA, Fax: +1(206)6858665   Email: lalic@chem.washington.edu
,
Richard P. Rucker
Department of Chemistry, University of Washington, Seattle, WA 98105, USA, Fax: +1(206)6858665   Email: lalic@chem.washington.edu
› Author Affiliations
Further Information

Publication History

Received: 07 October 2012

Accepted after revision: 13 November 2012

Publication Date:
12 December 2012 (online)

Abstract

A new procedure for direct transformation of alkenes to tertiary alkylamines based on hydroboration and copper-catalyzed amination of alkylboranes is described. The new method is presented in a broader context provided by a brief analysis of various approaches to the formation of anti-Markovnikov hydroamination products. A short discussion of the reaction development, scope, and the mechanism are also provided. Finally, the extension of this methodology to the preparation of hindered anilines from aryl ­boronic esters is presented.

 
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