- Silylation of O-H bonds by catalytic dehydrogenative and decarboxylative coupling of alcohols with silyl formates
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The silylation of O-H bonds is a useful methodology in organic synthesis and materials science. While this transformation is commonly achieved by reacting alcohols with reactive chlorosilanes or hydrosilanes, we show herein for the first time that silylformates HCO2SiR3 are efficient silylating agents for alcohols, in the presence of a ruthenium molecular catalyst.
- Chauvier, Clément,Godou, Timothé,Cantat, Thibault
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supporting information
p. 11697 - 11700
(2017/11/03)
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- A structurally simple self-immolative reagent that provides three distinct, simultaneous responses per detection event
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A general design is presented for a stimulus-responsive small molecule that is capable of responding to a specific applied chemical or physical signal by releasing two different types of pendant small molecules and a colorimetric indicator simultaneously. A key aspect of this design is the ease with which these reagents are prepared: typically, only four synthetic steps are required. Moreover, the modular construction strategy provides access to stimuli-responsive reagents that are capable of (i) responding to a variety of applied signals and (ii) releasing a number of different small molecules that contain primary alcohols, secondary alcohols, or phenols. These stimuli-responsive reagents are stable under physiological conditions (neither hydrolysis nor thermal degradation of the reagent occurs in significant quantity), and when they are exposed to the appropriate applied signal, they release both pendant small molecules and the colorimetric indicator completely within hours. Finally, unlike other functional groups, such as carbonates, that are used to connect alcohol-bearing molecules to controlled-release reagents, the linkage described in this article increases in hydrolytic stability (rather than decreases) as the pKa of the pendant alcohol decreases (Figure presented).
- Nunez, Sean A.,Yeung, Kimy,Fox, Nicole S.,Phillips, Scott T.
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experimental part
p. 10099 - 10113
(2012/02/05)
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- Efficient and convenient procedure for protection of hydroxyl groups to the THP, THF and TMS ethers and oxidation of these ethers to their aldehydes or ketones in [BPy]FeCl4 as a low cost room temperature ionic liquid
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Alcohols were converted to the corresponding THP, THF or TMS ethers in high to excellent yields in 1-n-butylpyridinium chloroferrate media as a stable and low cost room temperature ionic liquid. In addition, oxidation of these ethers to their aldehydes or ketones without any overoxidation reactions in this ionic liquid was also performed.
- Khosropour, Ahmad R.,Khodaei, Mohammad M.,Ghaderi, Sattar
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p. 326 - 330
(2007/10/03)
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- Yttrium-based Strong Lewis Acid Catalyst for Silylation of Alcohols with 1,1,1,3,3,3-Hexamethyldisilazane
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A variety of hydroxy compounds react with hexamethyldisilazane in the presence of a yttrium-based Lewis acid catalyst to afford the corresponding trimethylsilyl ethers in good to excellent yields.
- Kumar, Pradeep,Pais, Godwin C. G.,Keshavaraja
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p. 376 - 377
(2007/10/03)
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