- Carboxylation with CO2 via brook rearrangement: Preparation of α-hydroxy acid derivatives
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In the presence of CsF, a wide range of α-substituted α-siloxy silanes were carboxylated under a CO2 atmosphere (1 atm) via Brook rearrangement. A variety of α-substituents including aryl, alkenyl, and alkyl groups were tolerated to afford α-hydroxy acids in moderate-to-high yields. One-pot synthesis from aldehydes using PhMe2SiLi and CO 2 was also possible, providing α-hydroxy acids without the isolation of an α-hydroxy silane.
- Mita, Tsuyoshi,Higuchi, Yuki,Sato, Yoshihiro
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supporting information
p. 14 - 17
(2014/01/23)
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- Mg-promoted reductive coupling of aromatic carbonyl compounds with trimethylsilyl chloride and bis(chlorodimethylsilyl) compounds
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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).
- Uchida, Tetsuro,Kita, Yoshio,Maekawa, Hirofumi,Nishiguchi, Ikuzo
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p. 3103 - 3111
(2007/10/03)
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- Palladium or platinum complex catalysed reactions of carbonyl and imine compounds with disilanes
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The transition metal catalysed reactions of benzaldehydes and benzylideneamines with disilanes have been investigated. Palladium phosphine complexes catalyse the double silylation of the C=O bond in benzaldehydes and the C=N bond in benzylideneamines with
- Williams, Neil A.,Uchimaru, Yuko,Tanaka, Masato
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p. 236 - 243
(2007/10/03)
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- Mg-promoted reductive cross coupling of carbonyl compounds with trimethylsilyl chloride
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Mg-promoted cross-coupling of aromatic carbonyl compounds with trimethylsilyl chloride (TMSCl) in DMF at room temperature brought about reductive carbon-silicon bond formation to give the corresponding α-trimethylsilylalkyl trimethylsilyl ethers selectively in good yields.The reaction may be initiated through electron transfer from Mg metal to the carbonyl compounds.
- Ishino, Yoshi,Maekawa, Hirofumi,Takeuchi, Hiroshi,Sukata, Kazuaki,Nishiguchi, Ikuzo
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p. 829 - 830
(2007/10/03)
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- Electrochemical Reduction of Organic Compounds. 22. Preparation of Aromatic Aldehydes by Electroreduction of Esters and Amides in the Presence of Chlorotrimethylsilane
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The electroreduction of aromatic esters 1 and amides 9 in dry acetonitrile in the presence of chlorotrimethylsilane 2 affords aldehydes 3 in moderate to good yields depending on the aromatic substituents.The formation of 3 and characteristic by-products is discussed.
- Goetz-Schatowitz, P.-R.,Struth, G.,Voss, J.,Wiegand, G.
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p. 230 - 234
(2007/10/02)
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