A Tungsten–Tin Mixed Hydroxide as an Efficient Heterogeneous Catalyst for Dehydration of Aldoximes to Nitriles

Yamaguchi, Kazuya; Fujiwara, Hiroshi; Ogasawara, Yasushi; Kotani, Miyuki; Mizuno, Noritaka

doi:10.1002/anie.200605004

Cited by 190 publications

(59 citation statements)

References 29 publications

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“…Alternatively, nitriles are also synthesized by dehydration of aldoximes and this transformation has been widely studied. Various catalytic systems including CoCl 2 (15), KF/Al 2 O 3 (16), WÁSn hydroxide (17), ZnO/CH 3 COCl (18), metal triflates (19,20), clay (21), and zeolites (22), are reported for dehydration of aldoximes to nitriles. Some non-conventional techniques like use of microwaves (23,24) have also been reported.…”

Section: Introductionmentioning

confidence: 99%

Silica supported heteropolyacid catalyzed dehydration of aldoximes to nitriles and alcohols to alkenes

Parghi

Satam

Jayaram

2011

Green Chemistry Letters and Reviews

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An expedient method of silica supported heteropolyacid (HPA) catalyzed liquid phase dehydration of aldoxime to nitrile and secondary alcohols to alkenes were developed. Supported HPA was prepared by wet impregnation method and characterized by various analytical techniques such as X-ray diffraction, FT-IR, and NH 3 -TPD analysis. HPW-SiO 2 was found to be the most efficient catalyst amongst the prepared HPA and was found to be reusable for dehydration reaction under mild operating conditions giving high yields of the desired products.

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Section: Introductionmentioning

confidence: 99%

Silica supported heteropolyacid catalyzed dehydration of aldoximes to nitriles and alcohols to alkenes

Parghi

Satam

Jayaram

2011

Green Chemistry Letters and Reviews

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“…Besides the above-mentioned transformations, we have successfully developed several functional group transformations using hydroxide-based heterogeneous catalysts; for example, oxygenation and aromatization of alkylarenes 58) , oxidative homocoupling of 2-naphthols and substituted phenols 59) , N-alkylation of amines and NH3 using alcohols as the alkylation reagents 60), 61) , self-condensation of primary amines to secondary amines 62) , rearrangement of aldoximes to primary amides 63), 64) , and dehydration of aldoximes to nitriles 65) . Our hydroxide-based strategy demonstrated here has high generality and applications especially in the fields of catalytic chemistry and synthetic organic chemistry.…”

Section: Resultsmentioning

confidence: 99%

Supported Metal Hydroxides as Efficient Heterogeneous Catalysts for Green Functional Group Transformations

Yamaguchi

Mizuno

2014

J. Jpn. Petrol. Inst.

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This review article mainly describes our research on the development of highly active heterogeneous catalysts based on the properties of metal hydroxides and efficient green functional group transformations using these catalysts. Metal hydroxide species have both Lewis acid (metal center) and Brønsted base (hydroxy group) sites on the same metal sites. Combined action of the Lewis acid and Brønsted base paired sites can activate various types of organic substrates; for example, alcohols alkoxides, amines amides, nitriles η 2 -amidates, and terminal alkynes acetylides. In the presence of supported ruthenium hydroxide catalyst (Ru(OH)x/Al2O3), oxidative dehydrogenation of alcohols and amines efficiently proceeds, forming the corresponding carbonyl compounds (aldehydes and ketones) and nitriles, respectively. Ru(OH)x /Al2O3 can also catalyze hydration of nitriles to primary amides, ammoxidation of primary alcohols to nitriles, and formal α-oxygenation of primary amines to primary amides. In addition, oxidative alkyne homocoupling and 1,3-dipolar cycloaddition efficiently proceed in the presence of supported copper hydroxide catalysts (Cu(OH)x /OMS-2 for homocoupling, Cu(OH)x/TiO2 and Cu(OH)x/Al2O3 for cycloaddition; where OMS-2 is manganese oxide-based octahedral molecular sieve, KMn8O16). The catalytic processes for these transformations are heterogeneous, and the catalysts can be reused several times with maintained high catalytic activity.

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“…13). Besides the ruthenium catalyst, we have developed rhodium hydroxide (Rh(OH) x /Al 2 O 3 ) [89], copper hydroxide (Cu(OH) x /TiO 2 and Cu(OH) x / Al 2 O 3 ) [36,90], and tin-tungsten mixed hydroxide [91] catalysts for various heterogeneously catalyzed efficient functional group transformations. In this section, novel catalytic oxidative synthesis of nitriles (from primary alcohols and NH 3 ) [35] and amides (from primary amines) [34] by Ru(OH) x /Al 2 O 3 , and efficient oxidative homocoupling of alkynes by Cu(OH) x /TiO 2 [36] are mentioned.…”

Section: Aerobic Oxidations By Supported Metal Hydroxide Catalystsmentioning

confidence: 99%

Green Oxidation Reactions by Polyoxometalate-Based Catalysts: From Molecular to Solid Catalysts

2010

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This article summarizes our recent developments for H 2 O 2 -and O 2 -based green oxidation reactions by polyoxometalates (POMs) and related compounds. POMbased structurally controlled molecular catalysts exhibit high catalytic performance for epoxidation and sulfoxidation with H 2 O 2 . These molecular catalysts can be immobilized on the organic-inorganic hybrid support with covalently anchoring N-octyldihydroimidazolium cation fragments via the anion exchange. In addition, we have developed supported metal hydroxide catalysts such as Ru(OH) x /Al 2 O 3 and Cu(OH) x /TiO 2 on the basis of the information of the catalytically active sites with POMs. By using these supported metal hydroxide catalysts, novel aerobic oxidative synthesis of nitriles and amides, and efficient aerobic oxidative homocoupling of alkynes can be realized.

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A Tungsten–Tin Mixed Hydroxide as an Efficient Heterogeneous Catalyst for Dehydration of Aldoximes to Nitriles

Cited by 190 publications

References 29 publications

Silica supported heteropolyacid catalyzed dehydration of aldoximes to nitriles and alcohols to alkenes

Silica supported heteropolyacid catalyzed dehydration of aldoximes to nitriles and alcohols to alkenes

Supported Metal Hydroxides as Efficient Heterogeneous Catalysts for Green Functional Group Transformations

Green Oxidation Reactions by Polyoxometalate-Based Catalysts: From Molecular to Solid Catalysts

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