Multicomponent Strecker Reaction under High Pressure.

Matsumoto, Kiyoshi; Kim, Jong Chul; Iida, Hiroki; Hamana, Hiroshi; Kumamoto, Koji; Kotsuki, Hiyoshizo; Jenner, G.

doi:10.1002/chin.200546038

Cited by 2 publications

(3 citation statements)

References 10 publications

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“…However, there are not many examples for efficient and clean three-component Strecker reaction using diverse ketones including fluorinated ketones. Quite often, these reactions had to be carried out in two steps (preparation of imines followed by cyanide addition) or under high pressure . Our studies have revealed that Ga(OTf) 3 can act as an efficient catalyst for direct Strecker reaction of ketones with different types of amines and trimethylsilyl cyanide to afford the corresponding α-amino nitriles (precursors of α-amino acids) in high yields (Scheme ) .…”

Section: Multicomponent Reactions (Mcrs)mentioning

confidence: 99%

“…Quite often, these reactions had to be carried out in two steps (preparation of imines followed by cyanide addition) or under high pressure. 54 Our studies have revealed that Ga(OTf) 3 can act as an efficient catalyst for direct Strecker reaction of ketones with different types of amines and trimethylsilyl cyanide to afford the corresponding R-amino nitriles (precursors of R-amino acids) in high yields (Scheme 11). 55 Both aliphatic and aromatic ketones undergo ketonic Strecker reaction efficiently in the presence of Ga(OTf) 3 under mild conditions.…”

Section: Multicomponent Reactions (Mcrs)mentioning

confidence: 99%

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Gallium(III) Triflate: An Efficient and a Sustainable Lewis Acid Catalyst for Organic Synthetic Transformations

2011

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Green chemical processes play a crucial role in sustainable development, and efficient recyclable catalysts that can be conveniently applied in various chemical reactions are the key elements for the development of sustainable synthetic processes. Many organic transformations rely on Lewis and Brønsted acid catalysts, and such molecules have been widely studied in organic synthesis. Over the years, researchers have looked for Lewis acid catalysts that provide high selectivity and high turnover frequency but are also stable in aqueous media and recoverable. Since the first preparation of trifluoromethanesulfonic acid by Hazeldine (triflic acid, HOTf), researchers have synthesized and used numerous metal triflates in a variety of organic reactions. Even though the rare earth metal triflates have played a major role in these studies, the majority of rare earth triflates lack one or more of the primary properties of sustainable catalysts: low cost and easy availability of the metals, easy preparation of triflates, aqueous/thermal stability, recyclability, and catalytic efficiency. In this Account, we describe the synthetic applications of Ga(OTf)(3) and its advantages over similar catalysts. Ga(OTf)(3) can be conveniently prepared from gallium metal or gallium chloride in excess of trifluoromethanesulfonic acid (triflic acid) under reflux. Among many Lewis acid catalysts recently studied, Ga(OTf)(3) is water tolerant and soluble and requires very low catalyst loading to drive various acid-catalyzed reactions including Friedel-Crafts alkylation, hydroxyalkylation, and acylation selectively and efficiently. In many reactions Ga(OTf)(3) demonstrated high chemo- and regioselectivity, high yields, excellent stability, and recyclability. We successfully synthesized many biologically active heterocycles and their fluoroanalogs under mild conditions. Many challenging reactions such as the ketonic Strecker reactions proceed efficiently via Ga(OTf)(3) catalysis. Because it is stable in water, this catalyst provides the opportunity to study substrates and develop new synthetic protocols in aqueous media, significantly reducing the production of hazardous waste from organic solvents and toxic catalyst systems.

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Section: Multicomponent Reactions (Mcrs)mentioning

confidence: 99%

Section: Multicomponent Reactions (Mcrs)mentioning

confidence: 99%

Gallium(III) Triflate: An Efficient and a Sustainable Lewis Acid Catalyst for Organic Synthetic Transformations

2011

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“…Additionally, many of these catalysts are deactivated or decomposed by amines or the water produced during imine formation. Although a variety of profound modifications have been made to the original conditions, − the development of simple, efficient and general multicomponent procedures, utilizing ketones remains an unsolved challenge …”

Section: Introductionmentioning

confidence: 99%

Magnetic Solid Sulfonic Acid Decorated with Hydrophobic Regulators: A Combinatorial and Magnetically Separable Catalyst for the Synthesis of α-Aminonitriles

2014

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A three-component, Strecker reaction of a series of aldehydes or ketones, amines, and trimethylsilyl cyanide for the synthesis of α-aminonitriles in the presence of a catalytic amount of a magnetic solid sulfonic acid catalyst, Fe3O4@SiO2@Me&Et-PhSO3H under solvent-free conditions have been investigated. This catalyst, with a combination of hydrophobicity and acidity on the Fe3O4@SiO2 core-shell of the magnetic nanobeads, as well as its water-resistant property, enabled easy mass transfer and catalytic activity in the Strecker reaction. The catalyst was easily separated by an external magnet and the recovered catalyst was reused in 6 successive reaction cycles without any significant loss of activity.

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Multicomponent Strecker Reaction under High Pressure.

Cited by 2 publications

References 10 publications

Gallium(III) Triflate: An Efficient and a Sustainable Lewis Acid Catalyst for Organic Synthetic Transformations

Gallium(III) Triflate: An Efficient and a Sustainable Lewis Acid Catalyst for Organic Synthetic Transformations

Magnetic Solid Sulfonic Acid Decorated with Hydrophobic Regulators: A Combinatorial and Magnetically Separable Catalyst for the Synthesis of α-Aminonitriles

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