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Functionalization of octavinylsilsesquioxane by ruthenium-catalyzed silylative coupling versus cross-metathesis.
Chemistry. 2004 Mar 05; 10(5):1239-48.C

Abstract

Functionalization of octavinylsilsesquioxane (Vi(8)T(8), 1) by two reactions catalyzed by ruthenium complexes is reported: a silylative coupling reaction catalyzed by [RuHCl(CO)(PCy(3))(2)] (I) and cross-metathesis catalyzed by first- (II) and second-generation (III) Grubbs' catalysts. The two reactions of 1 with styrene take place highly regio- and stereoselectively (the X-ray structure of the product 2 has also been obtained); the cross-metathesis of 1-hexene and allyltrimethylsilane occurs quite effectively, whereas the silylative coupling with these compounds gives a mixture of isomers. Functionalization of 1 with heteroatom-substituted vinyl derivatives (Si, O, N) by silylative coupling reaction has been found to be highly efficient, but cross-metathesis appears to be the more effective method for the synthesis of S-substituted vinyl-silsesquioxane.

Authors+Show Affiliations

Itami Y
Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznan, Poland. marcinb@main.amu.edu.pl
Marciniec B
No affiliation info available
Kubicki M
No affiliation info available

MeSH

CatalysisMolecular StructureOrganometallic CompoundsRutheniumStereoisomerismVinyl Compounds

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

15007813

Citation

Itami, Y, et al. "Functionalization of Octavinylsilsesquioxane By Ruthenium-catalyzed Silylative Coupling Versus Cross-metathesis." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 10, no. 5, 2004, pp. 1239-48.
Itami Y, Marciniec B, Kubicki M. Functionalization of octavinylsilsesquioxane by ruthenium-catalyzed silylative coupling versus cross-metathesis. Chemistry. 2004;10(5):1239-48.
Itami, Y., Marciniec, B., & Kubicki, M. (2004). Functionalization of octavinylsilsesquioxane by ruthenium-catalyzed silylative coupling versus cross-metathesis. Chemistry (Weinheim an Der Bergstrasse, Germany), 10(5), 1239-48.
Itami Y, Marciniec B, Kubicki M. Functionalization of Octavinylsilsesquioxane By Ruthenium-catalyzed Silylative Coupling Versus Cross-metathesis. Chemistry. 2004 Mar 5;10(5):1239-48. PubMed PMID: 15007813.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Functionalization of octavinylsilsesquioxane by ruthenium-catalyzed silylative coupling versus cross-metathesis. AU - Itami,Y, AU - Marciniec,B, AU - Kubicki,M, PY - 2004/3/10/pubmed PY - 2004/12/16/medline PY - 2004/3/10/entrez SP - 1239 EP - 48 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 10 IS - 5 N2 - Functionalization of octavinylsilsesquioxane (Vi(8)T(8), 1) by two reactions catalyzed by ruthenium complexes is reported: a silylative coupling reaction catalyzed by [RuHCl(CO)(PCy(3))(2)] (I) and cross-metathesis catalyzed by first- (II) and second-generation (III) Grubbs' catalysts. The two reactions of 1 with styrene take place highly regio- and stereoselectively (the X-ray structure of the product 2 has also been obtained); the cross-metathesis of 1-hexene and allyltrimethylsilane occurs quite effectively, whereas the silylative coupling with these compounds gives a mixture of isomers. Functionalization of 1 with heteroatom-substituted vinyl derivatives (Si, O, N) by silylative coupling reaction has been found to be highly efficient, but cross-metathesis appears to be the more effective method for the synthesis of S-substituted vinyl-silsesquioxane. SN - 0947-6539 UR - https://www.unboundmedicine.com/medline/citation/15007813/Functionalization_of_octavinylsilsesquioxane_by_ruthenium_catalyzed_silylative_coupling_versus_cross_metathesis_ DB - PRIME DP - Unbound Medicine ER -