Facile synthesis of multifunctionalized allenes by magnesium-promoted reductive silylation of aromatic conjugated ynones

Mg-promoted reductive silylation of 4-phenyl-3-butyn-2-one in N,N-dimethylformamide (DMF) in the presence of chlorotrimethylsilane brought about double silylation at the β-carbon and oxygen atoms of the carbonyl group to give a multifunctionalized allene with a vinylsilane moiety and a silyl enol ether moiety. A variety of allenes can be synthesized through this simple methodology. Acid-catalyzed hydrolysis of an allene derived from the trimethylsilylation of 4-phenyl-3-butyn-2-one resulted in the formation of the corresponding benzalacetone with a trimethylsilyl group at the β-position of the carbonyl group in high yield.

Graphical abstractDownload full-size image