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84889354799
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Vinyl silanes are excellent ligands for late, low-valent transition metals. It has been suggested that the coordinating ability of vinyl silanes is mostly due to the Si-C=C (dp-pp) interaction, which allows delocalization of the alkene's electron density onto the silicon atom via its d-orbitals. This results in enhanced back-bonding between the metal centre and the olefin delocalized p* orbital. Therefore, greater thermal stability of the vinylsilane-containing complexes relative to their carbon analogues is observed
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Vinyl silanes are excellent ligands for late, low-valent transition metals. It has been suggested that the coordinating ability of vinyl silanes is mostly due to the Si-C=C (dp-pp) interaction, which allows delocalization of the alkene's electron density onto the silicon atom via its d-orbitals. This results in enhanced back-bonding between the metal centre and the olefin delocalized p* orbital. Therefore, greater thermal stability of the vinylsilane-containing complexes relative to their carbon analogues is observed.
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67
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84889310425
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Under "normal" conditions, the Pt complexes 14a to 14c are added to a mixture of silane 9 and olefin 10. The "inverse" protocol implies the addition of the silane 9 to a mixture of alkene 10 and Pt catalysts 14a to 14c. No colloidal Pt is formed upon increasing the amount of Pt-carbene catalysts from 30 up to 300 ppm. The rate increases concomitantly with the amount of catalyst, and the reaction can become highly exothermic
-
Under "normal" conditions, the Pt complexes 14a to 14c are added to a mixture of silane 9 and olefin 10. The "inverse" protocol implies the addition of the silane 9 to a mixture of alkene 10 and Pt catalysts 14a to 14c. No colloidal Pt is formed upon increasing the amount of Pt-carbene catalysts from 30 up to 300 ppm. The rate increases concomitantly with the amount of catalyst, and the reaction can become highly exothermic.
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68
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84889454931
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The high selectivity observed with this "inverse" procedure stems from the kinetics of the hydrosilylation reaction using (NHC)Pt(dvtms) complexes, which differ significantly from the Karstedt-catalyzed system. To obtain a fair comparison between the two catalysts, both reactions have been performed under identical, nonoptimized conditions
-
The high selectivity observed with this "inverse" procedure stems from the kinetics of the hydrosilylation reaction using (NHC)Pt(dvtms) complexes, which differ significantly from the Karstedt-catalyzed system. To obtain a fair comparison between the two catalysts, both reactions have been performed under identical, nonoptimized conditions.
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69
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84889293991
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Hydrosilylation of alcohol-containing substrates using the Karstedt catalyst results in significant formation of the corresponding silyl ethers (up to 40%)
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Hydrosilylation of alcohol-containing substrates using the Karstedt catalyst results in significant formation of the corresponding silyl ethers (up to 40%).
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70
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84889408774
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The high reactivity of the Karstedt catalyst precludes its use in the case of epoxide-bearing substrates. For example, more than 50% of vinyl cyclohexyl epoxide (Table 6.4, entry 5) is decomposed in the presence of this complex
-
The high reactivity of the Karstedt catalyst precludes its use in the case of epoxide-bearing substrates. For example, more than 50% of vinyl cyclohexyl epoxide (Table 6.4, entry 5) is decomposed in the presence of this complex.
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71
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84889284952
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Whilst most hydrosilylations are complete within 2-4 h, the reaction of allylacetone with 14b, under identical conditions, requires up to 24 h to reach 80% conversion (Table 6.4, entry 6). In the case of the platinum-carbene complex 14b, the catalyst is still active and prolonged reaction time leads to full conversion
-
Whilst most hydrosilylations are complete within 2-4 h, the reaction of allylacetone with 14b, under identical conditions, requires up to 24 h to reach 80% conversion (Table 6.4, entry 6). In the case of the platinum-carbene complex 14b, the catalyst is still active and prolonged reaction time leads to full conversion.
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72
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All the hydrosilylations performed using the carbene complex 10b afford crude products that are at least 95% pure and that typically contain less than 2% of isomerized alkene. With Karstedt catalyst 8, yellow solutions, including colloidal platinum species, are generated. The purity of the crude reaction mixtures varies between 72 and 92% and the amount of isomerized alkene oscillates between 5 and 11%. In the case of epoxide-containing substrates, extensive decomposition is observed
-
All the hydrosilylations performed using the carbene complex 10b afford crude products that are at least 95% pure and that typically contain less than 2% of isomerized alkene. With Karstedt catalyst 8, yellow solutions, including colloidal platinum species, are generated. The purity of the crude reaction mixtures varies between 72 and 92% and the amount of isomerized alkene oscillates between 5 and 11%. In the case of epoxide-containing substrates, extensive decomposition is observed.
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73
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84889278586
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It was necessary to heat for several hours at 60 °C complex 8 in the presence of the imidazolinium salt and KOtBu to obtain good yields of the desired complex
-
It was necessary to heat for several hours at 60 °C complex 8 in the presence of the imidazolinium salt and KOtBu to obtain good yields of the desired complex.
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The electronic effect of alkoxy groups on silicon does not correlate in a simple way with their electronegativity and their influence is difficult to rationalize
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The electronic effect of alkoxy groups on silicon does not correlate in a simple way with their electronegativity and their influence is difficult to rationalize.
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