Iron(III) tosylate-catalyzed deprotection of aromatic acetals in water

Olson, Margaret E.; Carolan, James P.; Chiodo, Michael V.; Lazzara, Phillip R.; Mohan, Ram S.

doi:10.1016/j.tetlet.2010.05.112

Cited by 16 publications

(6 citation statements)

References 28 publications

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“…Mohan and co-workers reported that aromatic acetals, both of aldehydes of and ketones, or α,β-unsaturated acetals were deprotected in the presence of a catalytic amount of iron(III) tosylate under mild conditions (Scheme 36). 97 A wide variety of acetal-protecting groups, including dimethyl or diethyl acetals and five-membered or six-membered cyclic acetals, were applicable. The authors noted the possibility that TSA might function as the true catalyst.…”

Section: Metal-based Catalystsmentioning

confidence: 99%

Catalytic Organic Reactions in Water toward Sustainable Society

et al. 2017

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Traditional organic synthesis relies heavily on organic solvents for a multitude of tasks, including dissolving the components and facilitating chemical reactions, because many reagents and reactive species are incompatible or immiscible with water. Given that they are used in vast quantities as compared to reactants, solvents have been the focus of environmental concerns. Along with reducing the environmental impact of organic synthesis, the use of water as a reaction medium also benefits chemical processes by simplifying operations, allowing mild reaction conditions, and sometimes delivering unforeseen reactivities and selectivities. After the "watershed" in organic synthesis revealed the importance of water, the development of water-compatible catalysts has flourished, triggering a quantum leap in water-centered organic synthesis. Given that organic compounds are typically practically insoluble in water, simple extractive workup can readily separate a water-soluble homogeneous catalyst as an aqueous solution from a product that is soluble in organic solvents. In contrast, the use of heterogeneous catalysts facilitates catalyst recycling by allowing simple centrifugation and filtration methods to be used. This Review addresses advances over the past decade in catalytic reactions using water as a reaction medium.

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Section: Metal-based Catalystsmentioning

confidence: 99%

Catalytic Organic Reactions in Water toward Sustainable Society

et al. 2017

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“…We explored this solvent for the synthesis of α‐aminonitrile, which gave us a 72 % yield in one hour (entry 7 of Table 1). The other solvents gave moderate yields (59 to 79 %) in 1 hour, whereas water was found to be the best solvent providing 92 % yield of the desired product in 30 min (entry 12 of Table 1), which could be due to the more solubility of the catalyst in water [17] …”

Section: Resultsmentioning

confidence: 97%

“…The other solvents gave moderate yields (59 to 79 %) in 1 hour, whereas water was found to be the best solvent providing 92 % yield of the desired in 30 min (entry 12 of Table 1), which could be due to the more solubility of the catalyst in water. [17] As the water was proved to be the best solvent, we further studied the catalytic load by using various catalytic amounts like without catalyst (0 mol%) to 15 mol% of catalyst in a water solvent. There was only 29 % (entry 8 of Table 1) of desired product formation without the catalyst, but by increasing the catalytic amount, the yield of the product also increased.…”

Section: Resultsmentioning

confidence: 99%

One‐Pot Synthesis of α‐Aminonitriles in Water Using Iron (III) Tosylate Hexahydrate (Fe(OTs)₃ ⋅ 6H₂O) as a Green Catalyst

Dave

Eeshwaraiah

2021

ChemistrySelect

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An efficient and environmentally friendly synthetic protocol has been presented to synthesize α‐aminonitriles from aldehydes, amines and trimethylsilyl cyanide using 10 mol% iron(III) tosylate hexahydrate (Fe(OTs)3 ⋅ 6H2O) as a green catalyst in aqueous media through one‐pot procedure. Iron(III) tosylate hexahydrate is a promising catalyst, introduced first time for the synthesis of α‐aminonitriles in aqueous media as it is commercially available, inexpensive, non‐toxic, operational simplicity and has a short reaction time with excellent yields is awaited to contribute to the development of novel green protocol for the synthesize α‐aminonitriles.

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“…[46][47][48][49] Recently, Tarannum and Siddiqui [50] reported a novel catalytic system, that consisted of Fe(OTs) 3 / SiO 2 , which was used for the multicomponent synthesis of the dibenzodiazepine analogues 29 (which contained only one benzene unit) under solvent-free conditions (Scheme 16). Its lack of sensitivity to moisture, ease in handling and low toxicity makes it an attractive catalyst for organic synthesis.…”

Section: Other Catalystsmentioning

confidence: 99%

Metal‐Catalyzed Routes to Dibenzodiazepines (DBDAs) and Structural Analogues: Recent Advances

2018

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It is common knowledge that the use of transition metals as catalysts has greatly revolutionized various coupling procedures to access heterocyclic compounds of significant industrial interest. Dibenzodiazepines (DBDAs) are a particularly important group of heterocyclic compounds, with considerable pharmaceutical applications. In this review, we look at some of the catalytic methods that have been developed during the last 10 years for the synthesis of these targets. Palladium catalysts have been frequently used for these transformations, and particularly for the Buchwald–Hartwig reaction which has been a key reaction in a number of synthetic pathways. Copper has also been frequently used, including some other metals like iron and molybdenum, but to a lesser extent. In most cases, the examples chosen are for the synthesis of DBDAs with interesting medicinal properties and will be of interest to medicinal chemists. It should also be mentioned that due to the structural characteristics of these compounds the potential for diversification – principally for functional group incorporation – is immense. Emerging and facilitating technologies have also been employed for the synthesis of these molecules and are reviewed here.

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Iron(III) tosylate-catalyzed deprotection of aromatic acetals in water

Cited by 16 publications

References 28 publications

Catalytic Organic Reactions in Water toward Sustainable Society

Catalytic Organic Reactions in Water toward Sustainable Society

One‐Pot Synthesis of α‐Aminonitriles in Water Using Iron (III) Tosylate Hexahydrate (Fe(OTs)₃ ⋅ 6H₂O) as a Green Catalyst

Metal‐Catalyzed Routes to Dibenzodiazepines (DBDAs) and Structural Analogues: Recent Advances

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Iron(III) tosylate-catalyzed deprotection of aromatic acetals in water

Cited by 16 publications

References 28 publications

Catalytic Organic Reactions in Water toward Sustainable Society

Catalytic Organic Reactions in Water toward Sustainable Society

One‐Pot Synthesis of α‐Aminonitriles in Water Using Iron (III) Tosylate Hexahydrate (Fe(OTs)3 ⋅ 6H2O) as a Green Catalyst

Metal‐Catalyzed Routes to Dibenzodiazepines (DBDAs) and Structural Analogues: Recent Advances

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One‐Pot Synthesis of α‐Aminonitriles in Water Using Iron (III) Tosylate Hexahydrate (Fe(OTs)₃ ⋅ 6H₂O) as a Green Catalyst