900258
Isopropoxy(phenyl)silane
别名:
RubenSilane
表单
liquid
质量水平
反应适用性
reagent type: reductant
reaction type: Reductions
折射率
n/D 1.4799
密度
0.926 g/mL
储存温度
2-8°C
SMILES字符串
[SiH2](OC(C)C)c1ccccc1
InChI
1S/C9H14OSi/c1-8(2)10-11-9-6-4-3-5-7-9/h3-8H,11H2,1-2H3
InChI key
XYMAHMLQCLMTDN-UHFFFAOYSA-N
一般描述
Isopropoxy(phenyl)silane is used as a stoichiometric reductant that allows for a significant decrease in catalyst loading, lower reaction temperatures, a wide range of functional group tolerance, and more diverse solvents in metal-catalyzed Mukaiyama hydrofunctionalizations.
应用
Isopropoxy(phenyl)silane can be used as a hydride source for alkene hydrofunctionalization reactions in the presence of metal catalysts, particularly under aprotic, nonalcoholic conditions. This reagent is considered as one of the most efficient stoichiometric reductants than phenylsilane because of its ability to exclude alcohol solvent from a series of catalytic reactions. When utilized, it allows the researcher to significantly decrease catalyst loadings, lower reaction temperatures, and employ more diverse solvents in iron- and manganese-catalyzed Mukaiyama hydrofunctionalizations.
It can be used as a reagent in:
It can be used as a reagent in:
- The hydrogenation of olefins
- Branch-selective olefin cross-coupling reactions
- Markovnikov alkene hydration/amination reactions
储存分类代码
10 - Combustible liquids
WGK
WGK 3
Isopropoxy (phenyl) silane
Demoret RM and Shenvi RA
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
Carla Obradors et al.
Journal of the American Chemical Society, 138(14), 4962-4971 (2016-03-18)
We report the discovery of an outstanding reductant for metal-catalyzed radical hydrofunctionalization reactions. Observations of unexpected silane solvolysis distributions in the HAT-initiated hydrogenation of alkenes reveal that phenylsilane is not the kinetically preferred reductant in many of these transformations. Instead
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