- Electron-Rich 0 = PR3 compounds: Catalysts for alcohol silylation
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The catalytic effect of a group of R3P = O compounds was studied in a mild procedure for the silylation of primary alcohols, secondary alcohols, hindered secondary alcohols, and of hindered phenols in the presence of t-butyldimethylsilyl chlori
- Liu, Xiaodong,Verkade, John G.
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- Synthetic Versatility of Lipases: Application for Si-O Bond Formation and Cleavage
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Several commercially available lipases were examined in a study on O-Si bond formation and cleavage applying silicon-based protecting groups and alcohols or the corresponding silyl ethers. With regard to deprotection, from silyl ether to the corresponding alcohol, only the solvent and the lipase were necessary. The influence of the protecting group, the lipase source, and the substituent was investigated to optimize the results. The TMS moiety could be removed in 24 hours of reaction at room temperature in aqueous systems (conv. up to 99%, depending on the substrate and lipase). The reverse reactions, that is, with the protection of the alcohols, were carried out in hexane using different silyl chlorides. The TMS, TES, and TBS moieties were successfully inserted in the primary and secondary alcohols without the need for dry conditions or an inert atmosphere, presenting conversions of up to 99%, depending on the substrate.
- Brondani, Patrícia Bulegon,Mittersteiner, Mateus,Voigt, Morgana Aline,Klinkowski, Bruna Heloisa,Riva Scharf, Dilamara,De Jesus, Paulo Cesar
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p. 477 - 485
(2019/01/10)
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- FLP-Catalyzed Transfer Hydrogenation of Silyl Enol Ethers
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Herein we report the first catalytic transfer hydrogenation of silyl enol ethers. This metal free approach employs tris(pentafluorophenyl)borane and 2,2,6,6-tetramethylpiperidine (TMP) as a commercially available FLP catalyst system and naturally occurring γ-terpinene as a dihydrogen surrogate. A variety of silyl enol ethers undergo efficient hydrogenation, with the reduced products isolated in excellent yields (29 examples, 82 % average yield).
- Khan, Imtiaz,Reed-Berendt, Benjamin G.,Melen, Rebecca L.,Morrill, Louis C.
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supporting information
p. 12356 - 12359
(2018/09/18)
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- Versatile dehydrogenative alcohol silylation catalyzed by Cu(I)-phosphine complex
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(Chemical Equation Presented) Cu(I) complexes of xanthane-based diphosphines were versatile catalysts for dehydrogenative alcohol silylation, exhibiting high activity and broad substrate scope. Highly selective silylation of 1-decanol over 2-decanol is possible even with a silylating reagent of small steric demand such as HSiMe2Ph or HSiEt3.
- Ito, Hajime,Watanabe, Akiko,Sawamura, Masaya
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p. 1869 - 1871
(2007/10/03)
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- Selective oxidation of benzylic alcohols and TBDMS ethers to carbonyl compounds with CrO3-H5IO6
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Benzyl alcohols and benzyl TBDMS ethers were efficiently oxidized to the corresponding carbonyl compounds in high yield with periodic acid catalyzed by CrO3 at low temperature (-78°C). The oxidation procedure was highly functional group tolerant and very selective for the TBDMS group over the TBDPS group. Georg Thieme Verlag Stuttgart.
- Zhang, Suhong,Xu, Liang,Trudell, Mark L.
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p. 1757 - 1760
(2007/10/03)
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