Tris sulfonium difluorotrimethylsilicate-Dimethylphenylsilane

Fluoride ion catalyzes the hydrosilylation of both alkyl and aryl aldehydes to silyl ethers that can be easily hydrolyzed to the free alcohols by treatment with 1 M hydrogen chloride in methanol.320 The most effective sources of fluoride are TBAF and tris(diethylamino)sulfonium difluorotrimethylsilicate (TASF). Somewhat less effective are CsF and KF. Solvent effects are marked. The reactions are facilitated in polar, aprotic solvents such as hexamethylphosphortriamide (HMPA) or 1,3-dimethyl-3,4,5,6-tetrahydro-2(l //)-pyrirnidinone (DMPU), go moderately well in dimethylformamide, but do not proceed well in either tetrahydrofuran or dichloromethane. The solvent effects are dramatically illustrated in the reaction of undecanal and dimethylphenylsilane to produce undecyloxyphenyldimethylsi-lane. After one hour at room temperature with TBAF as the source of fluoride and a 10 mol% excess of silane, yields of 91% in HMPA, 89% in DMPU, 56% in dimethylformamide, 9% in tetrahydrofuran, and only 1% in dichloromethane are obtained (Eq. 164).320... 

Dimethylphenylsilane Silane, dimethylphenyl- (8,9) (766-77-8)8 Tris(diethylamino)sulfonium difluorotrimethylsilicate Sulfur (1+), tris(N-ethyl-ethanaminato)-, difluorotrimethylsilicate (1-) (10) (59201-86-4) 1/treo-1-(3-Hydroxy-2-methy-3-phenylpropanoyl)piperidine, (R, S )- Piperidine, 1-(3-hydroxy-2-methyl-1-oxo-3-phenylpropyl)-, (R, S )- ( )- (11) (99114-35-9)... 

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See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ ]

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