Catalytic conversions in water. Part 10.† Aerobic oxidation of terminal olefins to methyl ketones catalysed by water soluble palladium complexes

Brink, Gerd‐Jan ten; Arends, Isabel W. C. E.; Papadogianakis, Georgios; Sheldon, Roger A.

doi:10.1039/a806532b

Cited by 99 publications

(30 citation statements)

References 19 publications

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“…These (phen)Pd(OAc) 2 complexes can be tuned to afford alcohol oxidation, [7] formation of hydrogen peroxide, [8] or Wacker-type reactions. [9] Recently, we proposed a catalytic cycle for the (phenS*)Pd(OAc) 2 -catalysed aerobic oxidation of alcohols in water (see Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Catalytic Conversions in Water. Part 22: Electronic Effects in the (Diimine)palladium(II)‐Catalysed Aerobic Oxidation of Alcohols

et al. 2003

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The electronic effects in the (diimine)Pd-(II)-catalysed aerobic oxidation of alcohols were investigated from the viewpoint of both the catalyst and the alcohol. A −push±pull× mechanism is operative, where both electron-donating substituents on the benzyl alcohol (1 À 0.58) and electron-withdrawing groups on the 4,4'-disubstituted-2,2'-bipyridine ligand (1 0.18) increase the reaction rate. The results indicate partial reduction of the palladium centre in the transition state of the rate-limiting step.

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Section: Introductionmentioning

confidence: 99%

Catalytic Conversions in Water. Part 22: Electronic Effects in the (Diimine)palladium(II)‐Catalysed Aerobic Oxidation of Alcohols

et al. 2003

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“…During the past decade, great progress has also been made in heterogeneous Pd catalysts for oxidation processes, for example, Pd/hydroxyapatite 17 , Pd/mesoporous silicas 18,19 polymer-supported Pd 20,21 , carbon nanotubesupported Pd 22,23 , Pd supported on metal oxide 24 , Pdcontaining metal-organic frameworks 25 etc. In the field of oxidation, the current Pd-based catalysis was focusing mainly on the oxidations associating with dehydrogenation processes (alcohol oxidation 26,27 , Wacker oxidation 28,29 , oxidative couplings 30 , etc.). The aerobic oxidation of hydrocarbons to more functional compounds (aldehydes, ketones, acids or esters), one of the most important processes in petrochemical transformation, has been seldom reported by Pd catalysts 31,32 .…”

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confidence: 99%

Solvent-free aerobic oxidation of hydrocarbons and alcohols with Pd@N-doped carbon from glucose

et al. 2013

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The development of efficient systems for selective aerobic oxidation of hydrocarbons and alcohols to produce more functional compounds (aldehydes, ketones, acids or esters) with atmospheric air or molecular oxygen is a grand challenge for the chemical industry. Here we report the synthesis of palladium nanoparticles supported on novel nanoporous nitrogendoped carbon, and their impressive performance in the controlled oxidation of hydrocarbons and alcohols with air. In terms of catalytic activity, these catalysts afford much higher turnover frequencies (up to 863 turnovers per hour for hydrocarbon oxidation and up to B210,000 turnovers per hour for alcohol oxidation) than most reported palladium catalysts under the same reaction conditions. This work provides great potential for the application of ambient air and recyclable palladium catalysts in fine-chemical production with high activity.

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“…A few examples of the ligand-modulated palladium-catalyzed oxidations of terminal alkenes into methyl ketones using molecular oxygen as the sole oxidant have been published. [9][10][11]14] Recently, Kaneda and co-workers have discovered that dimethylacetamide (DMA) as a solvent serves to stabilize a palladium catalyst preventing its precipitation into inactive metal and to promote a direct dioxygen-coupled Wacker oxidation of a number of terminal alkenes. [15] The system allows for an efficient catalytic turnover without the need for additional cocatalysts or special ligands under relatively mild conditions (80 8C, 6 atm of oxygen).…”

Section: Introductionmentioning

confidence: 99%

“…To overcome these problems, much effort has been devoted to the development of alternative halide-free co-catalysts, such as CuA C H T U N G T R E N N U N G (OAc) 2 , heteropoly acids, nitrates, and benzoquinone; [2][3][4][5][6][7][8] as well as, more recently, palladium catalysts modulated by special ligands. [8][9][10][11][12][13][14] In the latter systems, oxidatively robust (usually, nitrogen-containing) ligands are used to stabilize reduced palladium and promote its regeneration directly by molecular oxygen avoiding the use of corrosive additives. A few examples of the ligand-modulated palladium-catalyzed oxidations of terminal alkenes into methyl ketones using molecular oxygen as the sole oxidant have been published.…”

Section: Introductionmentioning

confidence: 99%

Palladium‐Catalyzed Oxidation of Phenyl‐Substituted Alkenes using Molecular Oxygen as the Sole Oxidant

2009

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The palladium-catalyzed aerobic oxidation of styrene and 2-vinylnaphthalene in dimethylacet-A C H T U N G T R E N N U N G amide/water or dimethylformamide/water solutions under mild conditions has been developed, in which palladium(II) chloride is used in the absence of cocatalysts or special stabilizing ligands as the sole and recyclable catalyst. The corresponding methyl ketones have been obtained in good to excellent yields with low catalyst loadings (0.2-5 mol%) and high turnover numbers (up to ca. 1000 to palladium). This simple and efficient catalytic method represents an ecologically benign and economically attractive synthetic pathway to industrially important compounds used in the manufacture of various polymers and drugs.

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Catalytic conversions in water. Part 10.† Aerobic oxidation of terminal olefins to methyl ketones catalysed by water soluble palladium complexes

Cited by 99 publications

References 19 publications

Catalytic Conversions in Water. Part 22: Electronic Effects in the (Diimine)palladium(II)‐Catalysed Aerobic Oxidation of Alcohols

Catalytic Conversions in Water. Part 22: Electronic Effects in the (Diimine)palladium(II)‐Catalysed Aerobic Oxidation of Alcohols

Solvent-free aerobic oxidation of hydrocarbons and alcohols with Pd@N-doped carbon from glucose

Palladium‐Catalyzed Oxidation of Phenyl‐Substituted Alkenes using Molecular Oxygen as the Sole Oxidant

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