Ytterbium Triflate: A Versatile Catalyst in Organic Synthesis

Zhang, Lang‐Jun; Lu, He‐Lin; Wu, Zhiping; Huang, Yanqi

doi:10.2174/138527281723131218135830

Cited by 10 publications

(3 citation statements)

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“…In fact, ytterbium trifluoride is a Lewis acid, as we have seen and as are other simple compounds of ytterbium (III) [1]. Both ytterbium (III) chloride [65] and ytterbium (III) triflate [66] are known to be Lewis acids, a property that underpins their widespread use as catalysts in organic chemistry. Typically, metal fluorides are stronger Lewis acids than their equivalent metal chlorides [67], which suggests that YbF 3 is likely to have considerable Lewis acidity.…”

Section: Ytterbium Fluoride In Dental Materialsmentioning

confidence: 77%

Ytterbium (III) Fluoride in Dental Materials

Nicholson

2023

Inorganics

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(1) Background: The compound ytterbium trifluoride is used as a component of several dental materials, and this is reviewed in the current article. (2) Methods: Published articles on this substance were identified initially from PubMed, and then from Science Direct and Google Scholar. The publications identified in this way showed that ytterbium trifluoride has been included in a variety of dental restorative materials, including composite resins, glass polyalkenoate cements, and calcium trisilicate cements. (3) Results: Ytterbium trifluoride is reported to be insoluble in water. Despite this, its presence is associated with fluoride release from dental materials. There is evidence that it reacts with the components of calcium trisilicate cements to form small amounts of a variety of compounds, including ytterbium oxide, Yb2O3, and calcium–ytterbium fluoride, CaYbF5. In nanoparticulate form, it has been shown to reinforce glass polyalkenoates and it also provides high contrast in X-ray images. (4) Conclusions: Ytterbium trifluoride is a useful component of dental materials, though some of the published findings suggest that there are aspects of its chemistry which are poorly understood.

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Section: Ytterbium Fluoride In Dental Materialsmentioning

confidence: 77%

Ytterbium (III) Fluoride in Dental Materials

Nicholson

2023

Inorganics

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“…It was obtained as colorless oil; yield (63, 0.086 g); R f (0.5% ethylacetate/hexane): 0.40. (8). It was obtained as colorless viscous liquid; yield (73%, 0.076 g); R f (20% ethylacetate/hexane): 0.70.…”

Section: -(Tert-butoxy)octane (2)mentioning

confidence: 99%

“…Overall, the rare-earth metal triflates served as a key that unlocked various catalytic reactions in the protection chemistry. However, no evidence for the use of Yb(OTf) 3 as a catalyst for the protection of alcohols to tert -butyl ethers was found despite its excellent utility in various reactions such as selective activation of aldimines over aldehyde for nucleophilic addition, diastereoselective radical cyclization, polymerization of methacrylate, cycloaddition and cyclization reactions, and so forth. , Yb(OTf) 3 has been used mostly in the catalytic deprotection studies such as selective deprotection of tert -butyl esters to carboxylic acids, selective deprotection of methoxyacetates and acetates to alcohols, and chemoselective deprotection of acetonide …”

Section: Introductionmentioning

confidence: 99%

Yb(OTf)₃-Catalyzed and Di-tert-butyl Dicarbonate-Mediated Decarboxylative Etherification and Esterification Reactions

et al. 2020

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Protecting group chemistry has invariably captured the fascination of chemists because of its extensive viability in chemical synthesis. The present report describes our pioneer work of applying ytterbium triflate as a catalyst, for the reaction of alcohols with di- tert -butyl dicarbonate (Boc 2 O) leading to the formation of tert -butyl ethers. There exists no recorded evidence for the use of Yb(OTf) 3 as a catalyst for the protection of alcohols to tert -butyl ethers, despite its excellent utility in various reactions. Yb(OTf) 3 has been used predominantly in the catalytic deprotection studies such as selective deprotection of tert -butyl esters to carboxylic acids as well as prenyl ethers to alcohols. This study involved the critical evaluation of solvent, time, and temperature that finally led to an efficient protocol for the formation of tert -butyl ethers. Yb(OTf) 3 catalyzed the formation of tert -butyl ethers, notably reducing the reaction time, which is exemplified by the achievement of up to 92% conversion of alcohols to tert -butyl ethers within an hour. Additionally, the report demonstrates the utility of this synthetic protocol for the protection of carboxylic acids.

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Mesoporous silica supported ytterbium as catalyst for synthesis of 1,2‐disubstituted benzimidazoles and 2‐substituted benzimidazoles

Samanta

Banerjee

Richards

et al. 2018

Applied Organom Chemis

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The benzimidazole ring is an important pharmacophore in contemporary drug discovery. Thus, effort to identifying new compounds containing benzimidazole scaffolds have gained much attention in recent years. In the present study, MCM‐41 type mesoporous silica with large pore (l‐MSN) supported ytterbium was successfully prepared by wet impregnation method. Among rare earth metal salts, ytterbium triflate has already been widely investigated as a catalyst in organic synthesis but less toxic ytterbium oxide has yet to be explored. Relatively high abundance and low cost of ytterbium with respect to many catalytically active metals (e.g. Pd, Au, Ru, Ir, Pt) offer an opportunity to develop sustainable catalysts for organic conversions. The catalyst has been characterized by various techniques including nitrogen adsorption, FT‐IR, TEM, SEM, EDX technique and elemental mapping. The obtained materials exhibit high surface area and a narrow distribution of mesoporosity. The catalytic performance of the Yb@l–MSNs was tested by synthesis of 1,2‐disubstituted benzimidazoles and 2‐substituted benzimidazoles through the coupling of aldehydes with o‐phenylenediamine. The catalyst resulted in excellent yields in short reaction times and the reaction showed tolerance toward both electron‐donating and electron‐withdrawing functional groups at room temperature. A particularly interesting finding was the solvent selectivity of this reaction; namely, 1,2‐disubstituted benzimidazoles generated as major product in water‐ethanol, while the 2‐substituted benzimidazoles was generated exclusively in non‐polar solvents like toluene.

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Ytterbium Triflate: A Versatile Catalyst in Organic Synthesis

Cited by 10 publications

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Ytterbium (III) Fluoride in Dental Materials

Ytterbium (III) Fluoride in Dental Materials

Yb(OTf)₃-Catalyzed and Di-tert-butyl Dicarbonate-Mediated Decarboxylative Etherification and Esterification Reactions

Mesoporous silica supported ytterbium as catalyst for synthesis of 1,2‐disubstituted benzimidazoles and 2‐substituted benzimidazoles

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Ytterbium Triflate: A Versatile Catalyst in Organic Synthesis

Cited by 10 publications

References 0 publications

Ytterbium (III) Fluoride in Dental Materials

Ytterbium (III) Fluoride in Dental Materials

Yb(OTf)3-Catalyzed and Di-tert-butyl Dicarbonate-Mediated Decarboxylative Etherification and Esterification Reactions

Mesoporous silica supported ytterbium as catalyst for synthesis of 1,2‐disubstituted benzimidazoles and 2‐substituted benzimidazoles

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Yb(OTf)₃-Catalyzed and Di-tert-butyl Dicarbonate-Mediated Decarboxylative Etherification and Esterification Reactions