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

Kanno, Ken‐ichiro; Noguchi, Seiya; Ono, Yukihiko; Egawa, Saki; Otsuka, Naoki; Mita, Masato; Kyushin, Soichiro

doi:10.1016/j.jorganchem.2021.122234

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Investigation Of Regio-and Diastereoselectivity1

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2024

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Cited by 7 publications

(1 citation statement)

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“…23,40,41 Recently, Kyushin reported Rucatalyzed (E)-or (Z)-selective hydrosilylation of alkynes and hydrooligosilanes without Si-Si bond cleavage. 29,42 We envisioned that (E)-selective addition of cyclosilanes to alkynes could yield s,p-conjugated cyclosilanes. As Kyushin's study focused on linear monohydrosilanes like H-SiMe 2 SiMe 2 -Ph, our initial focus was regioselectivity with tetrafunctional 1,4Si 6 (Table 1 and Fig.…”

Section: Investigation Of Regio-and Diastereoselectivitymentioning

confidence: 99%

Highly selective addition of cyclosilanes to alkynes enabling new conjugated materials

et al. 2022

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Section: Investigation Of Regio-and Diastereoselectivitymentioning

confidence: 99%

Highly selective addition of cyclosilanes to alkynes enabling new conjugated materials

et al. 2022

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Synthesis of Bis(alkenyl)oligosilanes via Double Hydrosilylation and Their Structures and Photophysical Properties

Kanno,

Kajima,

Suzuki

et al. 2024

Asian J Org Chem

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A series of novel bis(alkenyl)oligosilanes were synthesized via ruthenium‐catalyzed double hydrosilylation of alkynes with dihydrooligosilanes. The structural and photophysical features of the bis(alkenyl)oligosilanes were studied by X‐ray crystallography and UV and fluorescence spectra. The functional groups on the alkenyl moieties significantly affect not only their conformation and arrangement in crystals but also the UV and fluorescence spectra.

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Ruthenium‐Catalyzed Hydrosilylation of Aldehydes with Hydrooligosilanes

Kanno,

Sunaga,

Kyushin

2024

Zeitschrift anorg allge chemie

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Ruthenium‐catalyzed hydrosilylation of aldehydes with hydrooligosilanes is reported. Among the examined ruthenium catalysts, RuH2(CO)(PPh3)3 gave the best results. The reactions proceed with the Si–Si bonds preserved to afford the corresponding alkoxyoligosilanes in good yields. A series of aryl aldehydes with an electron‐withdrawing group is applicable, whereas those with an electron‐donating group are not suitable for the reaction. Mechanistic considerations suggest that the key points for the preservation of the Si–Si bonds are the formation of zero‐valent ruthenium species and the efficient coordination of the aldehyde to the ruthenium center prior to the oxidative addition of the Si–H bond.

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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

Cited by 7 publications

References 74 publications

Highly selective addition of cyclosilanes to alkynes enabling new conjugated materials

Highly selective addition of cyclosilanes to alkynes enabling new conjugated materials

Synthesis of Bis(alkenyl)oligosilanes via Double Hydrosilylation and Their Structures and Photophysical Properties

Ruthenium‐Catalyzed Hydrosilylation of Aldehydes with Hydrooligosilanes

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