A Synergic Blend of Newly Isolated Pseudomonas mandelii KJLPB5 and [hmim]Br for Chemoselective 2° Aryl Alcohol Oxidation in H2O2: Synthesis of Aryl Ketone or Aldehydes via Sequential Dehydration-Oxidative C=C Cleavage

Sharma, Nandini; Sharma, Upendra; Salwan, Richa; Kasana, Ramesh Chand; Sinha, Arun K.

doi:10.1007/s10562-010-0542-6

Cited by 6 publications

(2 citation statements)

References 35 publications

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“…Sinha and co-workers [59] investigated the oxidation of aryl alcohols utilizing Pseudomonas mandelii KJLPB5 and [hmim]Br in H 2 O 2 system. The carbonyl products could be prepared from either direct-oxidation or sequential dehydration-oxidation cleavage which led to the corresponding aryl aldehydes by losing some carbons from aryl alcohols.…”

Section: Oxidation Of Alcohols In Water Soluble Ionic Liquidsmentioning

confidence: 99%

“…For bromide anion ILs [59,60], 1-bromoalkane was gradually added in the mixture of 1-methylimidazole and toluene at room temperature under N 2 atmosphere. The reaction was carried out at 30-35 o C for 48 h. After that, the mixture was extracted with EtOAc /Et 2 O and solvents were removed by evaporation on rotary evaporator at 60 o C for 24 h. The yield of ILs obtained were above 90%.…”

Section: Preparation Of Water Soluble Ionic Liquidsmentioning

confidence: 99%

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Transformation of organic compounds by transition metal salts in ionic liquids

Taboonpong

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A new, convenient, and high yielding synthetic protocol for transformation via oxidation process of various organic compounds using a combination of 1-hexyl-3-methylimidazolium bromide ([hmim]Br) and a transition metal salt, such as FeCl3, and CuCl2 is uncovered. The oxidation of alcohols utilizing FeCl3/[hmim]Br in the presence of tert-butyl hydroperoxide (TBHP) afforded the corresponding carbonyl compounds in high yields. Primary and secondary benzylic alcohols seem to be reactive substrates for conversion to the desired carboxylic acids and ketones, respectively, without by-products formed. For aromatization of cyclic dienes catalyzed by CuCl2 coupled with TBHP in [hmim]Br, cyclic hydrocarbons yielded highly amount of the expected aromatic substances under short reaction time, while heterocyclic amines furnished the expected heteroaromatics in moderate yield. Consequently, the developed catalytic system of a transition metal salt/[hmim]Br displayed the reusability in this methodology. For the dehydrogenation of N-heterocycles, FeCl2/DMSO combination under oxygen atmosphere offered the corresponding N-heteroaromatic products in good yields via radical involving process, the catalytic system operated better under conventional organic solvents than ionic liquids.

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Section: Oxidation Of Alcohols In Water Soluble Ionic Liquidsmentioning

confidence: 99%

Section: Preparation Of Water Soluble Ionic Liquidsmentioning

confidence: 99%

Transformation of organic compounds by transition metal salts in ionic liquids

Taboonpong

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Thiol–Ene “Click” Reaction Triggered by Neutral Ionic Liquid: The “Ambiphilic” Character of [hmim]Br in the Regioselective Nucleophilic Hydrothiolation

et al. 2014

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Thiol–ene “click” chemistry has emerged as a powerful strategy to construct carbon–heteroatom (CS) bonds, which generally results in the formation of two regioisomers. To this end, the neutral ionic liquid [hmim]Br has been explored as a solvent cum catalyst for the synthesis of linear thioethers from activated and inactivated styrene derivatives or secondary benzyl alcohols and thiols without the requirement of using a metal complex, base, or free radical initiator. Furthermore, detailed mechanistic investigations using 1H NMR spectroscopy and quadrupole time‐of‐flight electrospray ionization mass spectrometry (Q‐TOF ESI‐MS) revealed that the “ambiphilic” character of the ionic liquid promotes the nucleophilic addition of thiol to styrene through an anti‐Markovnikov pathway. The catalyst recyclability and the extension of the methodology for thiol–yne click chemistry are additional benefits. A competitive study among thiophenol, styrene, and phenyl acetylene revealed that the rate of reaction is in the order of thiol–yne>thiol–ene>dimerization of thiol in [hmim]Br.

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Thiol–Ene “Click” Reaction Triggered by Neutral Ionic Liquid: The “Ambiphilic” Character of [hmim]Br in the Regioselective Nucleophilic Hydrothiolation

et al. 2014

Self Cite

View full text Add to dashboard Cite

Thiol-ene "click" chemistry has emerged as a powerful strategy to construct carbon-heteroatom (C-S) bonds, which generally results in the formation of two regioisomers. To this end, the neutral ionic liquid [hmim]Br has been explored as a solvent cum catalyst for the synthesis of linear thioethers from activated and inactivated styrene derivatives or secondary benzyl alcohols and thiols without the requirement of using a metal complex, base, or free radical initiator. Furthermore, detailed mechanistic investigations using (1)H NMR spectroscopy and quadrupole time-of-flight electrospray ionization mass spectrometry (Q-TOF ESI-MS) revealed that the "ambiphilic" character of the ionic liquid promotes the nucleophilic addition of thiol to styrene through an anti-Markovnikov pathway. The catalyst recyclability and the extension of the methodology for thiol-yne click chemistry are additional benefits. A competitive study among thiophenol, styrene, and phenyl acetylene revealed that the rate of reaction is in the order of thiol-yne>thiol-ene>dimerization of thiol in [hmim]Br.

show abstract

A Synergic Blend of Newly Isolated Pseudomonas mandelii KJLPB5 and [hmim]Br for Chemoselective 2° Aryl Alcohol Oxidation in H2O2: Synthesis of Aryl Ketone or Aldehydes via Sequential Dehydration-Oxidative C=C Cleavage

Cited by 6 publications

References 35 publications

Transformation of organic compounds by transition metal salts in ionic liquids

Transformation of organic compounds by transition metal salts in ionic liquids

Thiol–Ene “Click” Reaction Triggered by Neutral Ionic Liquid: The “Ambiphilic” Character of [hmim]Br in the Regioselective Nucleophilic Hydrothiolation

Thiol–Ene “Click” Reaction Triggered by Neutral Ionic Liquid: The “Ambiphilic” Character of [hmim]Br in the Regioselective Nucleophilic Hydrothiolation

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