Facile Synthesis Of Multifunctionalized Allenes By Magnesium-Promoted Reductive Silylation Of Aromatic Conjugated Ynones
TETRAHEDRON LETTERS(2014)
Abstract
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 beta-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 beta-position of the carbonyl group in high yield. (C) 2014 Elsevier Ltd. All rights reserved.
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Key words
Allenes,Reduction,Silylation,Magnesium,Conjugated ynone
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