New catalytic route to (E)-β-silyl-α,β-unsaturated ketones

(E)-β-(Silyl)-α,β-unsaturated ketones have been efficiently synthesized via one-pot sequential ruthenium-catalyzed silylative homo-coupling of dimethylphenylvinylsilane or trimethylvinylsilane (Marciniec coupling) and rhodium-catalyzed selective desilylative acylation (Narasaka coupling) of (E)-1,2-bis(silyl)ethenes with acid anhydrides. Synthetic strategy relies on the selective mono-substitution of the bis(silyl)ethene intermediate.

Graphical abstractNew catalytic route to (E)-β-silyl-α,β-unsaturated ketones.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► One-pot synthesis of (E)-β-silyl-β,β-unsaturated ketones from vinylsilanes. ► β-Silylketones are obtained by catalytic silylative coupling/acylation sequence. ► The strategy relies on the selective acylation of the bis(silyl)ethene intermediate.