Effect of catalysts on the reaction of allyl esters with hydrosilanes

Belyakova, Z. V.; Pomerantseva, M. G.; Efimova, L. A.; Chernyshev, E. A.; Стороженко, П. А.

doi:10.1134/s1070363210040079

Cited by 16 publications

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“…Allyl glycidyl ether is an important substrate because the alkoxysilanes derived from this alkene find broad applications in coatings and as coupling agents for epoxy composites employed for electronic chip encapsulation . However, hydrosilylation of allyl esters of this type using Pt catalysts are known to lead to side reactions . To our delight, the present nickel system is efficient for hydrosilylation of allyl glycidyl ether, giving 4 i in a 61 % yield.…”

Section: Figurementioning

confidence: 82%

An Easily Accessed Nickel Nanoparticle Catalyst for Alkene Hydrosilylation with Tertiary Silanes

2016

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The first efficient and non‐precious nanoparticle catalyst for alkene hydrosilylation with commercially relevant tertiary silanes has been developed. The nickel nanoparticle catalyst was prepared in situ from a simple nickel alkoxide precatalyst Ni(OtBu)2⋅x KCl. The catalyst exhibits high activity for anti‐Markovnikov hydrosilylation of unactivated terminal alkenes and isomerizing hydrosilylation of internal alkenes. The catalyst can be applied to synthesize a single terminal alkyl silane from a mixture of internal and terminal alkene isomers, and to remotely functionalize an internal alkene derived from a fatty acid.

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Section: Figurementioning

confidence: 82%

An Easily Accessed Nickel Nanoparticle Catalyst for Alkene Hydrosilylation with Tertiary Silanes

2016

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“…Then, we were interested in allyl-ether type substrates known for their difficulty to be selectively hydrosilylated as CQC isomerization and C-O cleavage were frequently observed. 27,28 In the case of phenyl allyl ether, the anti-Markovnikov product 3f was quantitatively yielded. The reactivity was slightly lower with butyl allyl ether and allyloxytrimethylsilane, yielding 70% and 77% of the hydrosilylation product, respectively (entries 7 and 8).…”

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confidence: 99%

Mn₂(CO)₁₀ and UV light: a promising combination for regioselective alkene hydrosilylation at low temperature

et al. 2022

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“…Next, we turned our interest to allyl-group-containing substrates, which are known to be notoriously difficult to selectively hydrosilylate as competing alkene isomerization, and C–O cleavage for allyl ethers − is frequently observed. Gratifyingly, hydrosilylation of allyloxytrimethylsilane leads to 86% of expected hydrosilylation product 3f along with a small amount of alkene isomerization (14%).…”

Section: Resultsmentioning

confidence: 99%

Developing a Highly Active Catalytic System Based on Cobalt Nanoparticles for Terminal and Internal Alkene Hydrosilylation

et al. 2020

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This work describes the development of easy to prepare cobalt nanoparticles (NPs) in solution as promising alternative catalysts for alkene hydrosilylation with the industrially relevant tertiary silane MD H M (1,1,1,3,5,5,5-heptamethyltrisiloxane). The Co NPs demonstrated high activity when used at 30 °C for 3.5-7 h in toluene, with catalyst loadings 0.05-0.2 mol%, without additives. Under these mild conditions, a set of terminal alkenes were found to react with MD H M, yielding exclusively the anti-Markovnikov product in up to 99% yields. Additionally, we demonstrated the possibility of using UV irradiation to further activate these cobalt NPs in order to enhance their catalytic performances, but also to promote tandem isomerization-hydrosilylation reactions using internal alkenes, among them unsaturated fatty ester (methyl oleate), to produce linear products in up to quantitative yields.

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Effect of catalysts on the reaction of allyl esters with hydrosilanes

Cited by 16 publications

References 0 publications

An Easily Accessed Nickel Nanoparticle Catalyst for Alkene Hydrosilylation with Tertiary Silanes

An Easily Accessed Nickel Nanoparticle Catalyst for Alkene Hydrosilylation with Tertiary Silanes

Mn₂(CO)₁₀ and UV light: a promising combination for regioselective alkene hydrosilylation at low temperature

Developing a Highly Active Catalytic System Based on Cobalt Nanoparticles for Terminal and Internal Alkene Hydrosilylation

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Effect of catalysts on the reaction of allyl esters with hydrosilanes

Cited by 16 publications

References 0 publications

An Easily Accessed Nickel Nanoparticle Catalyst for Alkene Hydrosilylation with Tertiary Silanes

An Easily Accessed Nickel Nanoparticle Catalyst for Alkene Hydrosilylation with Tertiary Silanes

Mn2(CO)10 and UV light: a promising combination for regioselective alkene hydrosilylation at low temperature

Developing a Highly Active Catalytic System Based on Cobalt Nanoparticles for Terminal and Internal Alkene Hydrosilylation

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Mn₂(CO)₁₀ and UV light: a promising combination for regioselective alkene hydrosilylation at low temperature