Facile synthesis of multifunctionalized allenes by magnesium-promoted reductive silylation of aromatic conjugated ynones |
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Authors: | Hirofumi Maekawa Atsushi TakanoMasamitsu Watanabe |
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Institution: | Department of Materials Science and Technology, Nagaoka University of Technology, 1603-1 Kamitomioka-cho, Nagaoka, Niigata 940-2188, Japan |
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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 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. |
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Keywords: | Allenes Reduction Silylation Magnesium Conjugated ynone |
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