Mg-promoted reductive coupling of aromatic carbonyl compounds with trimethylsilyl chloride and bis(chlorodimethylsilyl) compounds |
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Authors: | Tetsuro Uchida Hirofumi Maekawa |
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Institution: | a Department of Chemistry, Nagaoaka University of Technology, 1603-1 Kamitomioka, Nagaoka, Niigata 940-2188, Japan b Orient Chemical Industries, 8-1, Sanrahigashi-machi, Neyagawa, Osaka 572-8581, Japan |
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Abstract: | Mg-promoted reductive coupling of aromatic carbonyl compounds (1) with chlorosilanes, such as trimethylsilyl chloride (TMSCl:2), 1,2-bis(chlorodimethylsilyl)ethane (3) and 1,5-dichlorohexamethyltrisiloxane (4), in N,N-dimethylformamide (DMF) at room temperature brought about selective and facile reductive formation of both of carbon-silicon and oxygen-silicon bonds to give the corresponding α-trimethylsilylalkyl trimethylsilyl ethers (5) and cyclic siloxanes (6), (7) in moderate to good yields, respectively. The present facile and selective coupling may be initiated through electron transfer from Mg metal to aromatic carbonyl compounds (1). |
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Keywords: | Silylation Electron transfer Aromatic carbonyl compounds Magnesium |
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