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

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.