Tetrahydropyranylation of Alcohols over Modified Zeolites

Narender, Nama; Reddy, K. Suresh Kumar; Kumar, Macharla Arun; Rohitha, Chozhiyath Nappunni; Kulkarni, S. J.

doi:10.1007/s10562-009-0205-7

Cited by 27 publications

(10 citation statements)

References 22 publications

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“…Acid catalysts play a predominant role in organic synthesis, in particular tetrahydropyranylation. Due to its ease of handling and recovering, various solid acids were introduced, which include protic acids [2,3], Lewis acids [4,5], ion exchange resins [6,7], solid silica-based sulfonic acid [8], zeolites [9,10], hetropolyacids [11,12], and clays [13,14]. The main problems associated with solid acids are the complicated preparation procedure, corrosiveness, the expense, the harsh reaction conditions, the need for solvents such as CH 2 Cl 2 , as well as unsatisfactory product yields, etc.…”

Section: Introductionmentioning

confidence: 99%

Solvent-free tetrahydropyranylation of alcohols catalyzed by amine methanesulfonates

2010

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A comparative study of tetrahydropyranylation of alcohols under various solvents or solvent-free conditions using different amine methanesulfonates as catalysts shows that tetrahydropyranyl ethers of alcohols are obtained under solvent-free conditions in good yields using catalytic amounts of triethylenediamine methanesulfonate, 1,6-hexanediamine methanesulfonate, diethylenetriamine methanesulfonate and pyridine methanesulfonate, respectively. The reaction occurs readily in short times at room temperature catalyzed by these catalysts, especially triethylenediamine methanesulfonate. Some of the major advantages of this procedure are that the catalysts are environmentally friendly, highly effective, and easy to prepare and handle. The reaction is also clean and needs no solvent, and the work-up is very simple.

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Section: Introductionmentioning

confidence: 99%

Solvent-free tetrahydropyranylation of alcohols catalyzed by amine methanesulfonates

2010

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“…Tetrahydropyranylation reactions can be catalyzed by a number of different catalysts, like zeolites [31][32][33] , aluminum phosphates [34], sulfonated charcoal [35], polystyrene supported…”

Section: Catalytic Propertiesmentioning

confidence: 99%

Shape-selective organic–inorganic zeolitic catalysts prepared via interlayer expansion

et al. 2014

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Interlayer expansion of layered zeolite precursors is achieved via the insertion of an additional Tatom in between the layers, typically by means of a silylating agent as source of the T-atom. (3mercaptopropyl)methyldimethoxysilane was used as Si-source in the interlayer expansion of the layered zeolite precursors RUB-36 and RUB-39. The structure expansion was confirmed with PXRD. The incorporation of the silylating agent was followed with 29 Si MAS NMR, 13 C CP MAS NMR and thermogravimetric analysis. The incorporated thiol groups were oxidized with H2O2 to obtain sulphonic acid groups in between the layers. 13 C CP MAS NMR was used to characterize the organic species and monitor the conversion of thiol to propylsulphonic groups. The shapeselective properties of the obtained materials were investigated in acid-catalyzed tetrahydropyranylation reactions.

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“…Recently, metal oxides, ,[23,24,25,26] MOFs Ionic liquids and porous polymers ,[32,33,34,35] are also being explored for catalytic applications. Heterogeneous catalysts such as natural clays, ion‐exchange resins, silica‐based sulfonic acid, Fe 3 O 4 @SiO 2 @SO 3 H, polyaniline sulfate, carbon‐based solid acid, SiO 2 ‐ p ‐TSA, zeolites etc have been extensively investigated for tetrahydropyranylation of alcohols. However, many of the catalysts show lower catalytic activity except few catalysts which have shown exceptional catalytic activities.…”

Section: Introductionmentioning

confidence: 99%

Tuning Acidity of Sulfonated Mesoporous Polymers (MP−SO₃H) for Efficient Tetrahydropyranylation of Alcohols at Room Temperature

et al. 2020

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The sulfonated mesoporous polymers (MP−SO3H) with varying acidity were synthesized by template free solvothermal method followed by sulfonation at different intervals of time. The catalytic activities were tested for the tetrahydropyranylation of alcohols. Among the synthesized materials, MP−SO3H‐12 was found to be efficient and demonstrated the highest yield of pyranylated product which is superior in contrast to various heterogeneous catalysts screened. Furthermore, the substrate scope was extended to various primary, secondary, benzylic, aromatic, substituted aromatic and bulkier alcohol substrates. The catalyst retained its heterogeneity and there is no loss in its activity beyond three catalytic runs. The results observed herein are significant and comparable with the best reports available in the open literature. These interesting findings observed over MP−SO3H‐12 make it a potential candidate for the pyranylation of various alcohols under ambient reaction conditions.

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Tetrahydropyranylation of Alcohols over Modified Zeolites

Cited by 27 publications

References 22 publications

Solvent-free tetrahydropyranylation of alcohols catalyzed by amine methanesulfonates

Solvent-free tetrahydropyranylation of alcohols catalyzed by amine methanesulfonates

Shape-selective organic–inorganic zeolitic catalysts prepared via interlayer expansion

Tuning Acidity of Sulfonated Mesoporous Polymers (MP−SO₃H) for Efficient Tetrahydropyranylation of Alcohols at Room Temperature

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Tetrahydropyranylation of Alcohols over Modified Zeolites

Cited by 27 publications

References 22 publications

Solvent-free tetrahydropyranylation of alcohols catalyzed by amine methanesulfonates

Solvent-free tetrahydropyranylation of alcohols catalyzed by amine methanesulfonates

Shape-selective organic–inorganic zeolitic catalysts prepared via interlayer expansion

Tuning Acidity of Sulfonated Mesoporous Polymers (MP−SO3H) for Efficient Tetrahydropyranylation of Alcohols at Room Temperature

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Tuning Acidity of Sulfonated Mesoporous Polymers (MP−SO₃H) for Efficient Tetrahydropyranylation of Alcohols at Room Temperature