Mesoporous aluminosilicate-catalyzed allylation of carbonyl compounds and acetals

Ito, Suguru; Hayashi, Akira; Komai, Hirotomo; Yamaguchi, Hitoshi; Kubota, Yoshihiro; Asami, Masatoshi

doi:10.1016/j.tet.2011.01.055

Cited by 17 publications

(6 citation statements)

References 98 publications

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“…1-Allylcyclohexanol ( 5f ): 1 H-NMR (400 MHz, CDCl 3 ) δ 5.97–5.82 (m, 1H), 5.15 (m, 2H), 2.22 (d, J = 7.5 Hz, 2H), 1.72–1.37 (m, 10H), 1.35–1.21 (m, 1H). 13 C-NMR (101 MHz, CDCl 3 ) δ 133.7, 118.6, 70.9, 46.7, 37.4, 25.7, 22.2 [58].…”

Section: Methodsmentioning

confidence: 99%

A Green Approach for Allylations of Aldehydes and Ketones: Combining Allylborate, Mechanochemistry and Lanthanide Catalyst

et al. 2016

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Secondary and tertiary alcohols synthesized via allylation of aldehydes and ketones are important compounds in bioactive natural products and industry, including pharmaceuticals. Development of a mechanochemical method using potassium allyltrifluoroborate salt and water, to successfully perform the allylation of aromatic and aliphatic carbonyl compounds is reported for the first time. By controlling the grinding parameters, the methodology can be selective, namely, very efficient for aldehydes and ineffective for ketones, but by employing lanthanide catalysts, the reactions with ketones can become practically quantitative. The catalyzed reactions can also be performed under mild aqueous stirring conditions. Considering the allylation agent and its by-products, aqueous media, energy efficiency and use of catalyst, the methodology meets most of the green chemistry principles.

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Section: Methodsmentioning

confidence: 99%

A Green Approach for Allylations of Aldehydes and Ketones: Combining Allylborate, Mechanochemistry and Lanthanide Catalyst

et al. 2016

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“…1 Dec-1-en-4-ol (1m): [28] Following procedure A afforded 1m (35 % yield) as a colorless oil. 1 1-Cyclohexylbut-3-en-1-ol (1n): [27] Following procedure A afforded 1n (87 % yield) as a colorless oil. 1 Cyclohex-2-en-1-yl(phenyl)methanol (1o): [29] Following procedure A afforded 1o (56 % yield, 1:1 mixture of diastereomers) as a colorless oil.…”

Section: -(4-bromophenyl)but-3-en-1-ol (1c)mentioning

confidence: 99%

Green Organocatalytic Dihydroxylation of Alkenes

2017

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An inexpensive, green, metal‐free one‐pot procedure for the dihydroxylation of alkenes is described. H2O2 and 2,2,2‐trifluoroacetophenone were employed as the oxidant and organocatalyst, respectively, in this highly sustainable protocol in which a variety of homoallylic alcohols, aminoalkenes, and simple alkenes were converted into the corresponding polyalcohols in good to excellent yields. This process takes advantage of an epoxidation reaction followed by an acidic treatment in which water participates in the ring opening of the in situ prepared epoxide to lead to the desired product.

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“…A well‐known area of research for modern science involves incorporating a single or multiple transition and rare earth elements into the nanoscale structure of mesoporous materials, as well as into other frameworks. Mesoporous silica, carbon, zeolite, and metal‐organic frameworks containing various metal and metal oxides nanoparticles having a porous architecture, are highly recommended for various industrial uses including eco‐friendly catalytic transformations that depend on the properties of the present metals . In addition, these heteroatom‐loaded, highly‐ordered nanoporous materials have been extensively studied for other scientific applications, including biosensing, chemisorption, selective ion‐adsorption, specific drug delivery, photocatalysis, optoelectronics, magnetic devices, solar cells, fuel cells, and many more .…”

Section: Introductionmentioning

confidence: 99%

Ceria‐Containing Ordered Mesoporous Silica: Synthesis, Properties, and Applications

et al. 2015

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Structural architecture and unique physical, chemical, thermal, and mechanical properties of ordered mesoporous silica materials can be tuned. High flexibility of silica materials can provide good support for different metal nanoparticles, metal oxides, and organic functional groups. The properties of silica materials can vary to a great extent by introducing the optimum amount of metal species co‐doped, dispersed or composites with the silica mesostructure. The present study investigates the deposition of CeIII/IV/CeO2 on the silica surface by using different wet chemical engineering methods, illustrates the syntheses of those ceria–silica or metal doped ceria–silica nanomaterials and offers clear picture of the influence that incorporated ceria concentration has on the properties of the support material. Ceria–silica based ordered mesoporous materials can have numerous applications is also discussed in this article, emphasizing its use as a heterogeneous catalyst in particular.

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Mesoporous aluminosilicate-catalyzed allylation of carbonyl compounds and acetals

Cited by 17 publications

References 98 publications

A Green Approach for Allylations of Aldehydes and Ketones: Combining Allylborate, Mechanochemistry and Lanthanide Catalyst

A Green Approach for Allylations of Aldehydes and Ketones: Combining Allylborate, Mechanochemistry and Lanthanide Catalyst

Green Organocatalytic Dihydroxylation of Alkenes

Ceria‐Containing Ordered Mesoporous Silica: Synthesis, Properties, and Applications

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