Pyridine <i>N</i>‐Oxide Mediated Oxidation of Diarylalkynes with Palladium on Carbon

Sawama, Yoshinari; Takubo, Masato; Mori, Shigeki; Monguchi, Yasunari; Sajiki, Hironao

doi:10.1002/ejoc.201001641

Cited by 54 publications

(24 citation statements)

References 63 publications

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“…The same group found that pyridine N ‐oxide (replacing DMSO), an inexpensive and non‐toxic co‐oxidant, was efficient for the above oxidation reaction of 1,2‐diarylalkynes . Pyridine N ‐oxide plays three roles: (i) it acts as the oxygen source for the conversion of alkynes into diketones, (ii) it oxidizes Pd(0) to Pd(II), and (iii) it is the solvent.…”

Section: Applications Of Pd/cmentioning

confidence: 99%

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Development of the Applications of Palladium on Charcoal in Organic Synthesis

Liu

Astruc

2018

Adv Synth Catal

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Palladium on charcoal( Pd/C)h as lots of salient merits:( i) it is ac heap andc ommercial source of palladium, (ii)i ts hows efficientc atalytic activity even without ligands,( iii)a saheterogeneous catalyst it is easily recycledm any times by simple filtration,a nd (iv) it is applicablet oag reat number of reactions and substrates,a lthough it is eventually less efficient than homogeneous Pd catalysts containing some sophisticated ligands.T hisr eview recalls the main background ands ummarizes the progress made essentially during the last twelve years in Pd/C-catalyzed organic synthesis since the reviews by Felpins group andSekiin2 006.

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Section: Applications Of Pd/cmentioning

confidence: 99%

Section: Applications Of Pd/cmentioning

confidence: 99%

Development of the Applications of Palladium on Charcoal in Organic Synthesis

Liu

Astruc

2018

Adv Synth Catal

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“…While various synthetic methods for diketones from alkynes using halogenated oxidants, homogeneous transition metals, etc. have been developed, the heterogeneously catalyzed methods using additional oxidants are limited . Although the Pd/C‐catalyzed method with dimethyl sulfoxide (DMSO) as an oxidant and solvent has already been reported, homogeneous copper dichloride was required to promote the oxidation of alkynes …”

Section: Pd/c‐catalyzed Oxidation Of Alkynes To Diketonesmentioning

confidence: 99%

“…We have also been continuously investigating the development of green and sustainable organic reactions (e.g., deuteration, coupling reactions, and reduction) using heterogeneous platinum‐group metal catalysts supported on carbon and other novel functional and insoluble materials . We now summarize our recent research results about heterogeneous methods involving the oxidation of various organic and inorganic substances (internal alkynes, hydrogen gas, sulfides, and alcohols) using platinum‐group metals on carbon.…”

Section: Introductionmentioning

confidence: 99%

Versatile Oxidation Methods for Organic and Inorganic Substrates Catalyzed by Platinum-Group Metals on Carbons

Sawama

Asai

Monguchi

et al. 2015

The Chemical Record

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Platinum-group metals on activated carbon catalysts, represented by Pd/C, Ru/C, Rh/C, etc., are widely utilized to accomplish green and sustainable organic reactions due to their favorable features, such as easy handling, recoverability, and reusability. The efficient oxidation methods of various organic compounds using heterogeneous platinum-group metals on carbons with or without added oxidants are summarized in this Personal Account. The oxidation of internal alkynes into diketones was effectively catalyzed by Pd/C in the presence of dimethyl sulfoxide and molecular oxygen or pyridine N-oxide. The Pd/C-catalyzed mild combustion of gaseous hydrogen with molecular oxygen provided hydrogen peroxide, which could be directly utilized for the oxidation of sulfide derivatives into sulfoxides. Furthermore, the Ru/C-catalyzed aerobic oxidation of primary and secondary alcohols gave the corresponding aldehydes and ketones, respectively. On the other hand, the dehydrogenative oxidation of secondary alcohols into ketones was achieved using Rh/C in water, and primary alcohols were effectively dehydrogenated by Pd/C in water under mildly reduced pressure to produce carboxylic acids.

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“…We have previously reported the Pd/C‐catalyzed oxidations of alkynes to the corresponding 1,2‐diketones using oxygen gas (O 2 ) and dimethyl sulfoxide (DMSO) as the oxidants or pyridine N ‐oxide as an oxidant . For the general palladium‐catalyzed C−H functionalization reactions, the Pd(0) species would be generated after each catalytic reaction cycle, and the oxidation step should be required to reproduce the active Pd(II) species from Pd(0) .…”

Section: Introductionmentioning

confidence: 99%

Palladium on Carbon‐Catalyzed C−H Amination for Synthesis of Carbazoles and its Mechanistic Study

et al. 2016

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10% Palladium on carbon (10% Pd/C) successfully catalyzed the intramolecular C À Ha mination of various N-mesylated 2-aminobiphenyls in the presence of ac atalytic amount of pyridine Noxide in heated dimethyl sulfoxide (DMSO) under an oxygena tmosphere to afford the corresponding N-mesylcarbazoles.T he reactionw ould proceed via asingle-electron transfer process based on its significant suppression by the addition of as ingle-electron scavenger, tetracyanoquinodimethane (TCNQ), andt he substituents on the aromatic rings of the substrate have an insignificante ffect on the reaction progress.

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Pyridine N‐Oxide Mediated Oxidation of Diarylalkynes with Palladium on Carbon

Abstract: Pyridine N‐oxide works as an effective oxidant of 1,2‐diarylalkynes at 120 °C to form benzil derivatives under Pd/C‐catalyzed solvent‐free conditions, and Pd/C could be reused up to five times after simple filtration.

Cited by 54 publications

References 63 publications

Development of the Applications of Palladium on Charcoal in Organic Synthesis

Development of the Applications of Palladium on Charcoal in Organic Synthesis

Versatile Oxidation Methods for Organic and Inorganic Substrates Catalyzed by Platinum-Group Metals on Carbons

Palladium on Carbon‐Catalyzed C−H Amination for Synthesis of Carbazoles and its Mechanistic Study

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