A new method for the synthesis of amides from amines: Ruthenium tetroxide oxidation of N-protected alkylamines.

Tanaka, Kenichi; Yoshifuji, Shigeyuki; Nitta, Yoshihiro

doi:10.1248/cpb.36.3125

Cited by 100 publications

(43 citation statements)

References 2 publications

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“…An in situ generated (harmful) stoichiometric oxidant ruthenium(VIII) oxide has been utilized for such a reaction with N-tert-butoxycarbonyl protection of the amino group. 41 To the best of our knowledge, efficient homogeneous or heterogeneous catalytic oxygenations of primary amines to give amides had not been reported at the time of our work.…”

Section: Oxygenation Of Primary Amines To Give Amidesmentioning

confidence: 89%

Green Functional Group Transformations by Supported Ruthenium Hydroxide Catalysts

Yamaguchi¹,

Mizuno²

2010

Synlett

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This account summarizes our recent research on green functional group transformations using easily prepared supported ruthenium hydroxide catalysts [Ru(OH) x /support, support = Al 2 O 3 , TiO 2 , or Fe 3 O 4 ]. Various kinds of functional group transformations, e.g. the oxidation (oxidative dehydrogenation) of alcohols and amines, hydrogen-transfer reactions, such as racemization and reduction, and the hydration of nitriles, can be promoted by the concerted activation of the substrates (including alcohols, amines, and nitriles) by the Lewis acid and Brønsted base sites on the Ru(OH) x / support catalyst. In addition, we have successfully developed three novel catalytic transformations with the Ru(OH) x /support catalysts:(1) the oxygenation of primary amines to give amides, (2) the direct oxidative synthesis of nitriles from primary alcohols and ammonia, and (3) the N-alkylation of ammonia (or its surrogates) with alcohols to produce symmetrically substituted tertiary or secondary amines. The catalyses for these transformations are truly heterogeneous, and the catalysts retrieved after the transformations can be reused with retention of their high catalytic performance. 8 Conclusion

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Section: Oxygenation Of Primary Amines To Give Amidesmentioning

confidence: 89%

Green Functional Group Transformations by Supported Ruthenium Hydroxide Catalysts

Yamaguchi¹,

Mizuno²

2010

Synlett

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“…However, the efficiency of this methodology is rather limited owing to the high activation energy barrier and formation of organic waste products. Alternatively, amides can also be synthesized by oxidative amidation of aldehydes, rearrangement of aldoximes (Beckmann rearrangement, Scheme b), oxidative condensation of alcohols and amines (Scheme c), and oxygenation of α‐methylene group of amines (Scheme d) …”

Section: Amidesmentioning

confidence: 99%

Ruthenium‐Catalyzed Aerobic Oxidation of Amines

Ray

Hazari

Lahiri

et al. 2018

Chemistry An Asian Journal

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Amine oxidation is one of the fundamental reactions in organic synthesis as it leads to a variety of value-added products such as oximes, nitriles, imines, and amides among many others. These products comprise the key N-containing building blocks in the modern chemical industry, and such transformations, when achieved in the presence of molecular oxygen without using stoichiometric oxidants, are much preferred as they circumvent the production of unwanted wastes. In parallel, the versatility of ruthenium catalysts in various oxidative transformations is well-documented. Herein, this review focuses on aerobic oxidation of amines specifically by using ruthenium catalysts and highlights the major achievements in this direction and challenges that still need to be addressed.

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“…An environmentally friendly approach to the synthesis of amides is the direct oxygenation of primary amines. In general, it is very difficult to oxygenate primary amines to the corresponding amides and an in situ generated stoichiometric oxidant RuO 4 have been used with the N-Boc protection of amino groups [104]. As far as we know, efficient catalytic oxygenations of primary amines to amides including homogeneous as well as heterogeneous ones have never been reported.…”

Section: Novel Catalytic Oxidative Synthesis Of Amides From Primary Amentioning

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 new method for the synthesis of amides from amines: Ruthenium tetroxide oxidation of N-protected alkylamines.

Cited by 100 publications

References 2 publications

Green Functional Group Transformations by Supported Ruthenium Hydroxide Catalysts

Green Functional Group Transformations by Supported Ruthenium Hydroxide Catalysts

Ruthenium‐Catalyzed Aerobic Oxidation of Amines

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

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