Synfacts 2008(2): 0192-0192  
DOI: 10.1055/s-2007-992473
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Nickel-Catalyzed β-Boration ofα,β-Unsaturated Esters and Amides

Contributor(s): Paul Knochel, Tobias Thaler
K. Hirano, H. Yorimitsu*, K. Oshima*
Kyoto University, Japan
Further Information

Publication History

Publication Date:
23 January 2008 (online)

Significance

Although the β-boration of α,β-unsaturated aldehydes and ketones is a well-studied reaction, the boration of esters and amides, especially if they are sterically demanding, remains a difficult challenge. In this article the authors report an efficient method for the β-boration of various esters and amides with bis(pinacolato)diboron. This novel protocol, which involves Ni(cod)2 and PCy3 as catalytic system, grants an easy access to primary, secondary, and tertiary alkylboronates with ester and amide functionalities.