Palladium-Catalyzed Oxidation of Primary and Secondary Allylic and Benzylic Alcohols

Peterson, Karen L.; Larock, Richard C.

doi:10.1021/jo971268k

Cited by 340 publications

(99 citation statements)

References 42 publications

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“…Pd nanoparticles confined within such mesoporous silicas demonstrate good selectivity in crotyl and cinnamyl alcohol selox to their respective aldehydes ([70 %), and excellent TOFs of 7,000 and 5,000 h -1 for the respective alcohols. Similar activities are reported for secondary and tertiary allylic alcohols, highlighting the versatility of silica supported Pd nanoparticles [51,135,136,[180][181][182]. Incorporation of macropores into SBA-15 via dual hard/soft templating to Fig.…”

Section: Establishing Support Effectssupporting

confidence: 68%

Catalysing Sustainable Fuel and Chemical Synthesis

Lee¹

2015

Advanced Biofuels

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Concerns over the economics of proven fossil fuel reserves, in concert with government and public acceptance of the anthropogenic origin of rising CO 2 emissions and associated climate change from such combustible carbon, are driving academic and commercial research into new sustainable routes to fuel and chemicals. The quest for such sustainable resources to meet the demands of a rapidly rising global population represents one of this century's grand challenges. Here, we discuss catalytic solutions to the clean synthesis of biodiesel, the most readily implemented and low cost, alternative source of transportation fuels, and oxygenated organic molecules for the manufacture of fine and speciality chemicals to meet future societal demands.

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Section: Establishing Support Effectssupporting

confidence: 68%

Catalysing Sustainable Fuel and Chemical Synthesis

Lee¹

2015

Advanced Biofuels

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“…From the late 1990s, a number of homogeneous Pd-catalytic systems, such as Pd/coordinating solvent 9,10 , Pd/ligand [11][12][13][14][15] , have been investigated for aerobic oxidation. Compared with homogeneous catalysts, the heterogeneous catalysts, which are convenient for recycling from the reaction environment and readily used in flow reactors, are more popular, in particular in large-scale production 16 .…”

mentioning

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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“…The oxidation of the primary benzylic alcohols was strongly influenced by the electronic properties of Journal of Chemistry 13 the substituents on the benzyl group. In general, the oxidation rate of aromatic alcohols with electron-releasing groups was relatively higher than that of alcohols with electronwithdrawing group [13,97,98]. For instance, oxidation of an aromatic alcohol containing electron-donating group such 4-methoxylbenzyl alcohol gave 100% conversion only in 4 min (Table 6, entry 11), while oxidation of alcohol bearing electron-withdrawing group like 4-(trifluoromethyl)benzyl alcohol afforded 100% conversion within longer reaction time (8 min) ( Table 6, entry 13).…”

Section: Oxidation Of Different Types Of Alcohols Over 1%mentioning

confidence: 97%

Synthesis, Characterization, and Relative Study on the Catalytic Activity of Zinc Oxide Nanoparticles Doped MnCO₃, –MnO₂, and –Mn₂O₃ Nanocomposites for Aerial Oxidation of Alcohols

Assal

Kuniyil

Shaik

et al. 2017

Journal of Chemistry

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Zinc oxide nanoparticles doped manganese carbonate catalysts [ % ZnO x -MnCO 3 ] (where = 0-7) were prepared via a facile and straightforward coprecipitation procedure, which upon different calcination treatments yields different manganese oxides, that is, [ % ZnO x -MnO 2 ] and [ % ZnO x -Mn 2 O 3 ]. A comparative catalytic study was conducted to evaluate the catalytic efficiency between carbonates and oxides for the selective oxidation of secondary alcohols to corresponding ketones using molecular oxygen as a green oxidizing agent without using any additives or bases. The prepared catalysts were characterized by different techniques such as SEM, EDX, XRD, TEM, TGA, BET, and FTIR spectroscopy. The 1% ZnO x -MnCO 3 calcined at 300 ∘ C exhibited the best catalytic performance and possessed highest surface area, suggesting that the calcination temperature and surface area play a significant role in the alcohol oxidation. The 1% ZnO x -MnCO 3 catalyst exhibited superior catalytic performance and selectivity in the aerial oxidation of 1-phenylethanol, where 100% alcohol conversion and more than 99% product selectivity were obtained in only 5 min with superior specific activity (48 mmol⋅g −1 ⋅h −1 ) and 390.6 turnover frequency (TOF). The specific activity obtained is the highest so far (to the best of our knowledge) compared to the catalysts already reported in the literatures used for the oxidation of 1-phenylethanol. It was found that ZnO x nanoparticles play an essential role in enhancing the catalytic efficiency for the selective oxidation of alcohols. The scope of the oxidation process is extended to different types of alcohols. A variety of primary, benzylic, aliphatic, allylic, and heteroaromatic alcohols were selectively oxidized into their corresponding carbonyls with 100% convertibility without overoxidation to the carboxylic acids under base-free conditions.

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Palladium-Catalyzed Oxidation of Primary and Secondary Allylic and Benzylic Alcohols

Cited by 340 publications

References 42 publications

Catalysing Sustainable Fuel and Chemical Synthesis

Catalysing Sustainable Fuel and Chemical Synthesis

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

Synthesis, Characterization, and Relative Study on the Catalytic Activity of Zinc Oxide Nanoparticles Doped MnCO₃, –MnO₂, and –Mn₂O₃ Nanocomposites for Aerial Oxidation of Alcohols

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Palladium-Catalyzed Oxidation of Primary and Secondary Allylic and Benzylic Alcohols

Cited by 340 publications

References 42 publications

Catalysing Sustainable Fuel and Chemical Synthesis

Catalysing Sustainable Fuel and Chemical Synthesis

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

Synthesis, Characterization, and Relative Study on the Catalytic Activity of Zinc Oxide Nanoparticles Doped MnCO3, –MnO2, and –Mn2O3 Nanocomposites for Aerial Oxidation of Alcohols

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Synthesis, Characterization, and Relative Study on the Catalytic Activity of Zinc Oxide Nanoparticles Doped MnCO₃, –MnO₂, and –Mn₂O₃ Nanocomposites for Aerial Oxidation of Alcohols