Simple and Practical Aerobic Oxidation of Alcohols Catalyzed by a (&amp;lt;i&amp;gt;μ&amp;lt;/i&amp;gt;-Oxo)tetraruthenium Cluster

Kondo, Teruyuki; Kimura, Yu; Kanda, Takashi; Takagi, Daisuke; Wada, Kenji; Akio, Toshimitsu

doi:10.4236/gsc.2011.14023

Cited by 9 publications

(5 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Similar results (low yield of intermediate aldehyde) has been reported for oxidation of cylcohexanemethanol and other aliphatic alcohols. 36 Increasing the amount of catalyst (decreasing S/C ratio) does not always result in higher conversion (as observed for 1-phenyl-2-ethanol, entries 2 and 3 in Table S4). However, keeping the S/C ratio constant and increasing the amount of PTC (higher PTC/C ratio) lead to higher conversions (compare entries 2 and 4 in Table S4).…”

Section: ■ Introductionmentioning

confidence: 63%

See 1 more Smart Citation

Biphasic Catalytic Hydrogen Peroxide Oxidation of Alcohols in Flow: Scale-up and Extraction

Peer

Weeranoppanant

Adamo

et al. 2016

Org. Process Res. Dev.

View full text Add to dashboard Cite

We report continuous solvent-free biphasic alcohol oxidation with hydrogen peroxide and in-line separation of the tungsten polyoxometalate catalyst and phase transfer catalyst from the product. Zinc-substituted polyoxotungstate in combination with the selected phase transfer catalyst drives the oxidation reaction to completion within a short residence time (5−10 min) in a silicon Pyrex microreactor. This continuous and small-scale reactor allows for fast optimization of reaction conditions for each substrate and selection of the phase transfer catalyst. Scaling of the production rate (up to 650 times) is achieved with a Corning low flow reactor (LFR) and an advanced flow reactor (AFR). New scaled-up, in-line membrane-based liquid−liquid extraction units at the reactor outlet first separate the tungsten polyoxometalate catalyst with the aqueous waste stream from the organic product stream. A three-stage countercurrent liquid−liquid extraction then removes more than 90% of the phase transfer catalyst from the desired organic effluent stream while reducing the amount of extraction solvent required.

show abstract

Section: ■ Introductionmentioning

confidence: 63%

“…At high PTC concentration, the presence of excess catalytically active species and faster kinetic of the second oxidation step to carboxylic acid results in lower overall yield of aldehyde (entry 3). Similar results (low yield of intermediate aldehyde) has been reported for oxidation of cylcohexanemethanol and other aliphatic alcohols …”

Section: Resultsmentioning

confidence: 99%

Biphasic Catalytic Hydrogen Peroxide Oxidation of Alcohols in Flow: Scale-up and Extraction

Peer

Weeranoppanant

Adamo

et al. 2016

Org. Process Res. Dev.

View full text Add to dashboard Cite

show abstract

“…Our reported catalyst showed outstanding results for aliphatic amine (entry 6), which are generally less reactive and are reported to give low yields. 37,38 Similar to the alcohol oxidation reaction, the C−C double bond remains intact and oxidation of the nitrile group occurred selectively with the Ru@AAO catalyst for the oxidation of geranylamine (entry 7). Heteroatomic amines such as 2thiophene methylamine and indoline oxidized to desirable products under similar reaction conditions (entries 8 and 9).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Porous Anodic Aluminum Oxide as an Efficient Support for Ruthenium-Catalyzed Aerobic Oxidation of Alcohols and Amines

Hussain

Irshad

Haq

et al. 2019

Ind. Eng. Chem. Res.

View full text Add to dashboard Cite

The oxidation reactions of alcohols and amines to their respective aldehydes/ketones and nitriles are important reactions in the laboratory and industry. A highly robust and activated ruthenium-supported anodic aluminum oxide (Ru@AAO) has been synthesized through the sonochemical method. The sonochemical technique allowed a short synthesis time and uniform distribution of Ru on the AAO surface as confirmed by the scanning electron microscopy, transmission electron microscopy, X-ray diffraction analysis, and BET surface-area analysis. The synthesized catalyst was employed for the oxidation of alcohols and amines in the presence of atmospheric air at a relatively lower temperature. The synthesized catalyst showed excellent conversions of both alcohols and amines with high selectivities toward their respective aldehydes/ketones and nitriles. The function of the AAO support in Ru@AAO catalytic activity has also been elaborated in the present investigation.

show abstract

“…[5] Apart from the well-investigated nitrogen-based ligands, few organometallic complexes with phosphines have been applied to the oxidation of alcohols. [6] For example, palladium-catalyzed oxidations with tertiary phosphines, which have been used extensively in palladium-catalyzed crosscoupling reactions, are quite limited. [7] Clearly, the air sensitivity of most phosphines stays in sharp contrast to such ap-tion.…”

Section: Introductionmentioning

confidence: 99%

A Convenient and Selective Palladium‐Catalyzed Aerobic Oxidation of Alcohols

Gowrisankar

Neumann

Gördes

et al. 2013

Chemistry A European J

View full text Add to dashboard Cite

An efficient procedure for the oxidation of primary and secondary alcohols to aldehydes and ketones, respectively, with molecular oxygen under ambient conditions has been achieved. By applying catalytic amounts of Pd(OAc)2 in the presence of tertiary phosphine oxides (O=PR3) as ligands, a variety of substrates are selectively oxidized without formation of ester byproducts. Spectroscopic investigations and DFT calculations suggest stabilization of the active palladium(II) catalyst by phosphine oxide ligands.

show abstract

Simple and Practical Aerobic Oxidation of Alcohols Catalyzed by a (<i>μ</i>-Oxo)tetraruthenium Cluster

Cited by 9 publications

References 31 publications

Biphasic Catalytic Hydrogen Peroxide Oxidation of Alcohols in Flow: Scale-up and Extraction

Biphasic Catalytic Hydrogen Peroxide Oxidation of Alcohols in Flow: Scale-up and Extraction

Porous Anodic Aluminum Oxide as an Efficient Support for Ruthenium-Catalyzed Aerobic Oxidation of Alcohols and Amines

A Convenient and Selective Palladium‐Catalyzed Aerobic Oxidation of Alcohols

Contact Info

Product

Resources

About