- Utilization of a Trimethylsilyl Group as a Synthetic Equivalent of a Hydroxyl Group via Chemoselective C(sp3)-H Borylation at the Methyl Group on Silicon
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A conversion of trimethylsilylalkanes into the corresponding alcohols is established based on an iridium-catalyzed, chemoselective C(sp3)-H borylation of the methyl group on silicon. The (borylmethyl)silyl group formed by C(sp3)-H borylation is treated with H2O2/NaOH, and the resulting (hydroxymethyl)silyl group is converted into a hydroxyl group by Brook rearrangement, followed by oxidation of the resulting methoxysilyl group under Tamao conditions. An alternative route proceeding through the formylsilyl group formed from a (hydroxymethyl)silyl group by Swern oxidation is also established. The method is applicable to substituted trimethylsilylcycloalkanes and 1,1-dimethyl-1-silacyclopentane for conversion into the corresponding stereodefined cycloalkyl alcohols and 1,4-butanediol.
- Torigoe, Takeru,Ohmura, Toshimichi,Suginome, Michinori
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p. 2943 - 2956
(2017/03/23)
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- Method for Attachment of Silicon-Containing Compounds to a Surface and for Synthesis of Hypervalent Silicon-Compounds
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A method for inducing a hypervalent state within silicon-containing compounds by which they can be chemically attached to a surface or substrate and/or organized onto a surface of a substrate. The compounds when attached to or organized on the surface may have different physical and/or chemical properties compared to the starting materials.
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- ELECTROCHEMICAL OXIDATION OF ORGANOSILICON COMPOUNDS I. OXIDATIVE CLEAVAGE OF CARBON-SILICON BOND IN ALLYLSILANES AND BENZYLSILANES
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Electrochemical oxidation of allylsilanes and benzylsilanes in the presence of alcohol, carboxylic acid, or water resulted in cleavage of the carbon-silicon bond and formation of the corresponding ether, ester, or alcohol, respectively.
- Yoshida, Jun-ichi,Murata, Toshiki,Isoe, Sachihiko
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p. 3373 - 3376
(2007/10/02)
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