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Flores-Moreno, Jorge L.; Baraket, Leila; Figuéras, F.

doi:10.1023/a:1012795230177

Cited by 28 publications

(12 citation statements)

References 11 publications

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“…Examples of performant heterogeneous catalysts include Lewis acids immobilized on oxides, e.g. FeCl 3 , ZnCl 2 or H 3 BO 3 on TiO 2 nanoparticles [24] or Zn(CF 3 SO 3 ) 2 on hexagonal mesoporous silica (HMS) [23], sulfated alumina, titania or zirconia [25], titanium Beta zeolites [26] or mesoporous aluminosilicates [27]. Several MOFs have also been investigated for this reaction.…”

Section: Methodsmentioning

confidence: 99%

Counteranion effects on the catalytic activity of copper salts immobilized on the 2,2′-bipyridine-functionalized metal–organic framework MOF-253

et al. 2015

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The charge-neutral, aluminium-based metal-organic framework containing accessible 2,2-bipyridine (bpy) sites, MOF-253, is a suitable host material for the immobilization of various copper catalysts. The catalytic performance of CuCl 2 , Cu(NO 3) 2 , Cu(BF 4) 2 and Cu(CF 3 SO 3) 2 before and after coordination to the bpy ligands in MOF-253 was studied in the Meinwald rearrangement of ␣-pinene oxide to campholenic aldehyde (CA). The coordination environment of Cu 2+ in MOF-253 was further studied via EPR spectroscopy. Although the catalytic activity of the copper salts decreased upon heterogenization through coordination with the bpy linker, the selectivity to campholenic aldehyde markedly increased. Furthermore, the catalytic performance of the MOF loaded with copper salts was shown to vary greatly with the choice of charge compensating anion, allowing for improvement of the heterogeneous catalyst.

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Section: Methodsmentioning

confidence: 99%

Counteranion effects on the catalytic activity of copper salts immobilized on the 2,2′-bipyridine-functionalized metal–organic framework MOF-253

et al. 2015

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“…Alternative routes have been described using solid catalysts with Lewis acid sites giving high yield of campholenic aldehydes as shown in Table 2 [12][13][14][15] (Scheme 3).…”

Section: Catalytic Conversion Of Terpenesmentioning

confidence: 99%

Catalytic routes from renewables to fine chemicals

2007

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“…It is generally accepted that the formation of 2 is favored in the presence of Lewis acids, whereas Brønsted acids tend to produce a mixture of compounds in low yields, such as trans-carveol (3), trans-sobrerol (4 a), and p-cymene. [6,[8][9][10] Various solid Lewis acids have been used as catalysts for the isomerization of a-pinene oxide into aldehyde 2; [6,8,[10][11][12][13][14] however, most of these reactions are time-consuming and/or involve high catalyst/substrate ratios.…”

Section: Introductionmentioning

confidence: 99%

Phosphotungstic Acid as a Versatile Catalyst for the Synthesis of Fragrance Compounds by α‐Pinene Oxide Isomerization: Solvent‐Induced Chemoselectivity

Rocha

Hoehne

Gusevskaya

2008

Chemistry A European J

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The remarkable effect of the solvent on the catalytic performance of H3PW12O40, the strongest heteropoly acid in the Keggin series, allows direction of the transformations of alpha-pinene oxide (1) to either campholenic aldehyde (2), trans-carveol (3), trans-sobrerol (4 a), or pinol (5). Each of these expensive fragrance compounds was obtained in good to excellent yields by using an appropriate solvent. Solvent polarity and basicity strongly affect the reaction pathways: nonpolar nonbasic solvents favor the formation of aldehyde 2; polar basic solvents favor the formation of alcohol 3; whereas in polar weakly basic solvents, the major products are compounds 4 a and 5. On the other hand, in 1,4-dioxane, which is a nonpolar basic solvent, both aldehyde 2 and alcohol 3 are formed in comparable amounts. The use of very low catalyst loading (0.005-1 mol %) and the possibility of catalyst recovery and recycling without neutralization are significant advantages of this simple, environmentally benign, and low-cost method. This method represents the first example of the synthesis of isomers from alpha-pinene oxide, other than campholenic aldehyde, with a selectivity that is sufficient for practical usage.

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Untitled

Cited by 28 publications

References 11 publications

Counteranion effects on the catalytic activity of copper salts immobilized on the 2,2′-bipyridine-functionalized metal–organic framework MOF-253

Counteranion effects on the catalytic activity of copper salts immobilized on the 2,2′-bipyridine-functionalized metal–organic framework MOF-253

Catalytic routes from renewables to fine chemicals

Phosphotungstic Acid as a Versatile Catalyst for the Synthesis of Fragrance Compounds by α‐Pinene Oxide Isomerization: Solvent‐Induced Chemoselectivity

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