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

Abstract

The 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.

Key words

allenes - copper - esters - nitriles - silylboranes

Publication History

Received: 28 August 2021

Accepted after revision: 20 September 2021

Accepted Manuscript online:
20 September 2021

Article published online:
19 October 2021

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