Copper-Catalyzed Regioselective Sila-acylation and Sila-imination of Allenes Using Esters and Nitriles

Abstract

AbstractThe sila-acylation of allenes is performed in the presence of a copper catalyst using PhMe2Si-B(pin) and esters as the silyl and acyl sources, respectively. β-Silyl-β,γ-unsaturated ketones are obtained regioselectively in good to high yields. The sila-imination of allenes is also achieved using nitriles as electrophiles. Exposure of the reaction mixture to air results in the production of cyclic silyl peroxides.