Ruthenium-catalyzed hydrosilylation of alkynes with preservation of the Si–Si bond of hydrooligosilanes: Regio- and stereoselective synthesis of (Z)-alkenyloligosilanes and carbonyl-functionalized alkenyldisilanes

•Ruthenium-catalyzed Z-selective hydrosilylation of alkynes with hydrooligosilanes is reported.•A deuterium labeling experiment suggests the existence of a vinylideneruthenium species.•Carbonyl-functionalized alkenyloligosilanes were synthesized regio- and stereoselectively. Ruthenium-catalyzed Z-se...

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Bibliographic Details
Published in:Journal of organometallic chemistry 2022-03, Vol.961, p.122234, Article 122234
Main Authors: Kanno, Ken-ichiro, Noguchi, Seiya, Ono, Yukie, Egawa, Saki, Otsuka, Naoki, Mita, Masato, Kyushin, Soichiro
Format: Article
Language:English
Subjects:
Hydrooligosilane
Hydrosilylation
Ruthenium catalyst
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Summary:•Ruthenium-catalyzed Z-selective hydrosilylation of alkynes with hydrooligosilanes is reported.•A deuterium labeling experiment suggests the existence of a vinylideneruthenium species.•Carbonyl-functionalized alkenyloligosilanes were synthesized regio- and stereoselectively. Ruthenium-catalyzed Z-selective hydrosilylation of alkynes afforded alkenyloligosilanes with high regio- and stereoselectivity without Si–Si bond cleavage. Among examined catalysts, RuHCl(CO)(PPh3)(dppp) was found to be the most suitable for the Z-selective hydrosilylation. A deuterium labeling experiment suggests the existence of a vinylideneruthenium species which is the key intermediate for the Z-selectivity. By using this method as well as previously reported E- and α-selective hydrosilylation, (E)-, (Z)- and α-alkenyldisilanes bearing carbonyl functionality were selectively synthesized. [Display omitted]
ISSN:0022-328X
1872-8561
DOI:10.1016/j.jorganchem.2021.122234