Highly active and selective platinum(0)-carbene complexes. Efficient, catalytic hydrosilylation of functionalised olefins

Advanced Synthesis and Catalysis

Volumn 346, Issue 12, 2004, Pages 1429-1434

  Markó, István E ^a   Stérin, Sébastien ^a   Buisine, Olivier ^a   Berthon, Guillaume ^a   Michaud, Guillaume ^a   Tinant, Bernard ^a   Declercq, Jean Paul ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

Alkenes; Homogeneous catalysis; Hydrosilylation; N heterocyclic carbenes; Platinum

Indexed keywords

ALKENE DERIVATIVE; CARBENOID; PLATINUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROSILYLATION; ISOMERIZATION; SYNTHESIS;

EID: 9144232015     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404048     Document Type: Article

References (36)

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25. Vi-Pt-Ccarb-N = 98°.
26. Hydrosilylation of alcohol-containing substrates using the Karstedt catalyst results in significant formation of the corresponding silyl ethers (up to 40%).
27. 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 2, Entry 5) is decomposed in the presence of this complex.
28. While most hydrosilylations are complete within 2-4 h, the reaction of allylacetone with 10b, under identical conditions, requires up to 24 h to reach 80% conversion. In the case of the platinum-carbene complex 10b, the catalyst is still active and prolonged reaction time leads to full conversion.
29. All the hydrosilylations performed using the carbene complex 10b afford crude products which are at least 95% pure and which typically contain less than 2% of isomerised alkene. With Karstedt catalyst 8, yellow solutions, including colloidal platinum species, are generated. The purity of the crude reaction mixture varies between 72-92% and the amount of isomerised alkene oscillates between 5-11%. In the case of epoxide-containing substrates, extensive decomposition is observed.
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36. For the preparation and structure determination of the analogous phosphine-containing dimers, see: M. Ciriano, M. Green, J. A. K. Howard, J. Proud, J. L. Spencer, G. A. F. Stone, C. A. Tsipis, J. Chem. Soc. Dalton Trans. 1978, 801; for the hydrosilylation of alkenes using these dimers, see: M. Green, J. L. Spencer, G. A. F. Stone, C. A. Tsipis, J. Chem. Soc. Dalton Trans. 1977, 1519.