Ruthenium-catalyzed selective hydrosilylation reaction of allyl-functionalized PEG derivatives

[Display omitted] •Selective hydrosilylation of allyl-functionalized PEGs was achieved.•The reactions were achieved using simple ruthenium catalyst, [RuCl2(nbd)]n.•This method can be applied to synthesis of various functionalized-PEG-materials. Reactions of allyl-functionalized poly(ethylene glycol)...

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Veröffentlicht in:Tetrahedron letters 2019-10, Vol.60 (41), p.151086, Article 151086
Hauptverfasser: Inomata, Koya, Naganawa, Yuki, Guo, Haiqing, Sato, Kazuhiko, Nakajima, Yumiko
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Sprache:eng
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Zusammenfassung:[Display omitted] •Selective hydrosilylation of allyl-functionalized PEGs was achieved.•The reactions were achieved using simple ruthenium catalyst, [RuCl2(nbd)]n.•This method can be applied to synthesis of various functionalized-PEG-materials. Reactions of allyl-functionalized poly(ethylene glycol) (PEG) derivatives with alkoxysilanes proceeded efficiently to furnish the corresponding hydrosilylated products in good to excellent yields using a ruthenium catalyst, [RuCl2(nbd)]n. A preliminary mechanistic study supported the pivotal role of the PEG moiety, which coordinated to the ruthenium atom during the reaction to achieve high reaction selectivity. This method may be applicable to the synthesis of various PEGs with a silyl terminus, which is useful as biocompatible and low toxic silane coupling agents.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2019.151086