Reduction of heterocyclic carboxaldehydes via Meerwein–Ponndorf–Verley reaction

Jiménez‐Sanchidrián, César; Hidalgo, José Manuel Soto; Ruíz, José Rafael

doi:10.1016/j.apcata.2006.01.035

Cited by 32 publications

(11 citation statements)

References 38 publications

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“…Finally, hydrotalcite-like catalysts have also been successfully used in the MPV reduction of heterocyclic carbonyl compounds [71,72] and sulphur-containing aldehydes [72], which is a substantial advance as sulphur is a major poison for the metal catalysts typically used in the conventional reduction with hydrogen gas. …”

Section: Mpv Reduction Over Hydrotalcitesmentioning

confidence: 99%

Heterogeneous Catalysis in the Meerwein-Ponndorf-Verley Reduction of Carbonyl Compounds

Ruíz¹,

Jiménez‐Sanchidrián

2007

COC

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The Meerwein-Ponndorf-Verley (MPV) reaction involves the catalysed transfer of hydrogen from an alcohol to a carbonyl compound and provides an effective method for synthesizing carbonyl compounds under very mild conditions. The method, which requires the use of a catalyst, is high selective as it leaves most reducible functional groups in the carbonyl reactant untouched. The classical MPV reaction is conducted in a homogeneous phase, usually in the presence of a metal alkoxide as catalyst. The process has been extensively studied over the past 15 years, using heterogeneous catalysts that minimize or avoid many of the problems inherent in homogeneous catalysis. The most widely used among such catalysts consist of metal oxides (particularly aluminium, magnesium and zirconium oxides), magnesium phosphates, layered double hydroxides, mesoporous solids and zeolitic compounds. These materials vary widely in nature and include acid, basic, neutral, mesoporous and microporous solids. This allows virtually any type of carbonyl compound to be reduced by using an appropriate available catalyst. This paper reviews the most salient advances in MPV reduction processes involving heterogeneous catalysts, with emphasis of the reaction proper rather than on the nature of the catalyst. Special attention is given to the shape selectivity provided by zeolitic materials and layered double hydroxides for some carbonyl compounds.

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Section: Mpv Reduction Over Hydrotalcitesmentioning

confidence: 99%

Heterogeneous Catalysis in the Meerwein-Ponndorf-Verley Reduction of Carbonyl Compounds

Ruíz¹,

Jiménez‐Sanchidrián

2007

COC

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“…These include a large variety of different compounds, but the use of metal oxides and grafted alkoxides seems to be the most promising alternative. Among these materials, those based on zirconium as the active species [9] have received much attention because of the extraordinary activity showed by this metal in MPV hydrogen-transfer reactions, for its high resistance against water deactivation, and for the easiness in which this heteroatom can be heterogenized onto solid supports [10,11]. In this way, zirconium-functionalized heterogeneous catalysts used in MPV transformations comprise a large variety of solids, including hydrous zirconia [9,[12][13][14] both supported onto other supports like silica and as bulk material, zirconium-functionalized silicas [12][13][14] and zirconium-containing zeolites [15][16][17][18][19], most of them based on the BEA structure.…”

Section: Introductionmentioning

confidence: 99%

Zr-SBA-15 Lewis Acid Catalyst: Activity in Meerwein Ponndorf Verley Reduction

et al. 2015

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Zr-SBA-15 Lewis acid catalyst has demonstrated an outstanding catalytic activity in the reduction of several carbonyl compounds by means of Meerwein Ponndorf Verley (MPV) reaction, using several secondary alcohols, and showing a very high selectivity towards the desired products. Special focus was addressed in the catalytic activity of Zr-SBA-15 material in the production of furfuryl alcohol from furfural, which is an important reaction for the lignocellulosic biomass valorization. In this transformation, both the reaction temperature and the i-PrOH:Furfural molar ratio exert a positive influence on the rate of the MPV transformation, with the influence of the former being much higher.i-propyl-furfuryl ether, a by-product resulting from the etherification of the target product with the sacrificing alcohol, is also found together with the main product. The production of this side-product is highly influenced by the reaction temperature, so that low temperatures and high sacrificing alcohol to substrate molar ratios have to be applied to keep its production at low levels.

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“…This necessitates its separation downstream and moisture sensitivity limit is another drawback to overcome. A number of heterogeneous catalysts have also been considered for this reaction, to name: Sn-, Ti-, Zr-and Al-beta-zeolites [2,3], magnesium oxide [4,5], Mg/Al hydroxides [6][7][8], zirconia and metal modified zirconia [9][10][11]. Zirconium and aluminium propoxide supported on mesostructured silicas were also found to be active in the reduction carbonyl compounds [12][13][14].…”

Section: Introductionmentioning

confidence: 99%