76622-52-1

Upstream product

• 40299-93-2 rac-isopropylmethoxymethylphenylsilane 
• 75-30-9 2-iodo-propane 
• 766-08-5 methylphenylsilane 
• 3027-21-2 dimethoxy(methyl)phenylsilane 

Downstream Products

• 40299-93-2 rac-isopropylmethoxymethylphenylsilane 
• 56-33-7 1,1,3,3-tetramethyl-1,3-diphenyldisiloxane 
• 104617-07-4 dichloromethylisopropylmethylphenylsilane 
• 1273594-99-2 rac-3-isopropylmethylphenylsilyl-1-methylindole 
• 98-85-1 1-Phenylethanol 
• 133407-14-4 methylphenylisopropylchlorosilane 
• 1273594-97-0 C₂₆H₃₈OSi 
• 1273594-98-1 C₂₆H₃₈OSi 
• 1273594-96-9 (SiRS)-isopropylmethylphenyl[(-)-8-phenylmenthyloxy]silane 
• 79628-17-4 heptylisopropylmethylphenylsilane 

Relevant academic research and scientific papers

Insight into the mechanism of carbonyl hydrosilylation catalyzed by brookharts cationic iridium(iii) pincer complex

New experimental findings suggest partial revision of the currently accepted mechanism of the carbonyl hydrosilylation catalyzed by the iridium(III) pincer complex introduced by Brookhart. Employing silicon-stereogenic silanes as a stereochemical probe results in racemization rather than inversion of the configuration at the silicon atom. The degree of the racemization is, however, affected by the silane/carbonyl compound ratio, and inversion is seen with excess silane. Independently preparing the silylcarboxonium ion intermediate and testing its reactivity then helped to rationalize that effect. The stereochemical analysis together with these control experiments, rigorous multinuclear NMR analysis, and quantum-chemical calculations clearly prove that another silane molecule participates in the hydride transfer. The activating role of the silane is unexpected but, in fact, vital for the catalytic cycle to close.

B(C6F5)3-Catalyzed reduction of ketones and imines using silicon-stereogenic silanes: Stereoinduction by single-point binding

We recently employed a silicon-stereogenic silane as a stereochemical probe to clarify the mechanism of the B(C6F5) 3catalyzed hydiosilylation of ketones. When using a prochiral ketone, reasonable stereoinduction was seen, originating from the stereogenicity at the silicon atom, a chirality transfer from silicon to carbon through single-point binding of the chiral silane to the carbonyl oxygen atom. In the present investigation, we further elaborated on this remarkable observation by systematic variation of the ketone substitution pattern. We then included prochiral imines as well to test for diastereocontrol. Unexpectedly, these substance classes, ketones and imines, yielded diametrically opposed results in the reduction with a silicon-stereogenic silane. While the level of diastereoselection was decent in the C=O reduction (dr ≈ 80:20), no asymmetric induction was detected in the C=NR reduction. On the basis of these experimental data and our previous mechanistic insight, we propose different reaction pathways for the reduction step of these related B(C6F 5)3 catalyses. Aside from these mechanistic implications, we also report an unusual 1,6- rather than conventional 1,2-reduction of a sterically encumbered diaryl-substituted ketone.

Selective synthesis of monohydrosilanes by the reactions of organoytterbium iodides with dihydrosilanes

Monohydrosilanes can be prepared selectively in high yields from the reaction of various aryl and alkyl iodides with ytterbium metal followed by the reaction with dihydrosilanes.

ASYMMETRIC INDUCTION BY CHIRAL SILICON GROUPS

The reduction of racemic RPhMeSiCCl2CH3 systems (R=cyclohexyl, isoprpyl, t-butyl and 2-mesityl) to the diastereomeric RPhMeSiCHClCH3 with tributyltin hydride was used as a probe into the potential of the RPhMeSi group to induce asymmetry at an α position.Favorable results were obtained for R=mesityl.