Highly efficient alcohol oxidation catalyzed by palladium(II)–alkylamine complexes using atmospheric molecular oxygen

Shimazu, Shogo; Uehara, Tae; Asami, Aki; Hara, Takayoshi; Ichikuni, Nobuyuki

doi:10.1016/j.molcata.2007.10.036

Cited by 15 publications

(6 citation statements)

References 20 publications

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“…23 The peaks at 6.2-6.6 ppm are attributed to hydrogen in amido groups. 24,25 The peaks at 9.3-9.5 ppm assigned to hydrogen in aldehyde groups 26,27 and the relative peak area increase along with the amount of isobutyraldehyde, which coincide with the results of FTIR. The probability of the reaction shown in Scheme 4 increases on increasing the amount of isobutyraldehyde.…”

Section: H-nmrsupporting

confidence: 75%

Synthesis and structural characterization of urea–isobutyraldehyde–formaldehyde resins

2008

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Urea-isobutyraldehyde-formaldehyde (UIF) resins were synthesized using urea, isobutyraldehyde, and formaldehyde; sulfuric acid was used as a catalyst. The effects of molar ratio of urea/isobutyraldehyde/ formaldehyde (U/I/F) on the properties of resins were investigated, and the structures of the resins were characterized by FTIR, 1 H-NMR, and 13 C-NMR. When U/I/F was 1.0/3.6/2.4, the yield of the resin was 76.5%. The softening point and hydroxyl value were 90°C and 32 mg KOH/g, respectively. The FTIR, 1 H-NMR, and 13 C-NMR results showed that an a-ureidoalkylation reaction occurred between urea and isobutyraldehyde to form a lactam. The UIF resins also contained hydroxyl groups and aldehyde groups; the content of aldehyde groups in the resin increased as the amount of isobutyraldehyde increased.

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Section: H-nmrsupporting

confidence: 75%

Synthesis and structural characterization of urea–isobutyraldehyde–formaldehyde resins

2008

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“…Similar reaction conditions to those used for the secondary aliphatic alcohols in Table 3, entry 3 (Chart 1) were used for the aliphatic primary alcohol. The desired heptadecanoic acid (10) was obtained in a yield of 7%; however, 50% of unreacted (9) remained. A trace amount of hexadecane (12) was detected in the reaction mixture using 1 H-NMR and GC/MS.…”

Section: Resultsmentioning

confidence: 99%

“…The oxidation of alcohols is one of the most fundamental molecular transformation reactions. In comparison to oxidation methods using stoichiometric amounts of oxidative reagents (such as pyridinium chlorochromate, 1,2) Dess-Martin periodinane, 3) manganese dioxide, 4,5) and so on [6][7][8] ), catalytic aerobic [9][10][11][12][13][14][15][16][17] and dehydrogenative alcohol oxidation reactions [18][19][20][21][22][23] are environmentally-friendly organic syntheses in which less residual reactants (such as oxidants) are generated. In green chemistry, solvent-free reactions are advantageous because they decrease environmental waste, avoid the emission of organic solvents, and allow for down-scaling of the reaction vessels.…”

Section: Introductionmentioning

confidence: 99%

Ruthenium-on-Carbon-Catalyzed Facile Solvent-Free Oxidation of Alcohols: Efficient Progress under Solid–Solid (Liquid)–Gas Conditions

et al. 2021

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“…1 was efficiently stabilized by exerting the steric effect [21] of a secondary diamine ligand bearing n ‐hexadecyl groups at both nitrogen donor atoms. Amines featured by long aliphatic chains have been efficiently used in Pd‐based hydrogenation, [22] Suzuki Miyaura coupling [23,24] and aerobic alcohol oxidation reactions [25] . 1 has been used to catalyze the aerobic oxidation of 1,2‐PD in n ‐hexane and supported onto a high surface area carbon in neutral water.…”

Section: Introductionmentioning

confidence: 99%

“…Amines featured by long aliphatic chains have been efficiently used in Pd-based hydrogenation, [22] Suzuki Miyaura coupling [23,24] and aerobic alcohol oxidation reactions. [25] 1 has been used to catalyze the aerobic oxidation of 1,2-PD in n-hexane and supported onto a high surface area carbon in neutral water.…”

Section: Introductionmentioning

confidence: 99%

Selectivity Switch in the Aerobic 1,2‐Propandiol Oxidation Catalyzed by Diamine‐Stabilized Palladium Nanoparticles

et al. 2021

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Palladium nanoparticles stabilized by a sterically demanding secondary diamine ligand have been synthesized by hydrogen reduction of a palladium acetate complex bearing the corresponding diimine ligand. The obtained nanoparticles were used to catalyze the aerobic oxidation of 1,2‐propandiol in n‐hexane, and after their heterogenization onto a high surface area carbon, in water. In n‐hexane (2,4‐dimethyl‐1,3‐dioxolan‐2‐yl) methanol has been obtained as major product, whereas in water acetic acid with a selectivity of >85 % has been achieved. The selectivity switch observed was a clear induced by water. The robustness of diamine‐stabilized palladium nanoparticles under real aerobic oxidation conditions has been proved by recycling experiments, TEM measurements of the recovered catalysts and by comparison of its performance with that of palladium nanoparticles generated by the metal vapor synthesis technique and supported onto the same carbon in the absence of the stabilizing diamine ligand.

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Highly efficient alcohol oxidation catalyzed by palladium(II)–alkylamine complexes using atmospheric molecular oxygen

Cited by 15 publications

References 20 publications

Synthesis and structural characterization of urea–isobutyraldehyde–formaldehyde resins

Synthesis and structural characterization of urea–isobutyraldehyde–formaldehyde resins

Ruthenium-on-Carbon-Catalyzed Facile Solvent-Free Oxidation of Alcohols: Efficient Progress under Solid–Solid (Liquid)–Gas Conditions

Selectivity Switch in the Aerobic 1,2‐Propandiol Oxidation Catalyzed by Diamine‐Stabilized Palladium Nanoparticles

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