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

Abstract

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