100-06-1Relevant articles and documents
Regeneration of carbonyl compounds by oxidative cleavage of oximes with NBS in the presence of β-cyclodextrin in water
Reddy, M. Somi,Narender,Rao, K. Rama
, p. 3875 - 3881 (2004)
The conversion of different oximes to the corresponding carbonyl compounds was carried out at room temperature in good to high yields with N-bromosuccinimide in water in the presence of β-cyclodextrin.
First example of water-soluble transition-metal catalysts for Oppenauer-type oxidation of secondary alcohols
Ajjou, Abdelaziz Nait
, p. 13 - 16 (2001)
The first water-soluble transition-metal catalysts for Oppenauer-type oxidation of secondary alcohols have been developed. The catalytic system composed of [Ir(COD)Cl]2, 2,2'-biquinoline-4,4'-dicarboxylic acid dipotassium salt (BQC) and sodium carbonate is highly efficient for the selective oxidation of benzylic and aliphatic secondary alcohols to the corresponding ketones with catalyst/substrate ratios ranging from 0.4 to 2.5 percent. The substitution of [Ir(COD)Cl]2 by its rhodium analog [Rh(COD)Cl]2 generates a less active catalytic system. [Ir(COD)Cl]2/BQC was also found to be more active than its water-insoluble analog system [Ir(COD)Cl]2/2,2'-biquinoline (BC).
Nickel boride mediated cleavage of 1,3-oxathiolanes: A convenient approach to deprotection and reduction
Khurana, Jitender M.,Magoo, Devanshi,Dawra, Kiran
, p. 1113 - 1116 (2016)
1,3-Oxathiolanes are rapidly cleaved by nickel boride allowing regeneration of corresponding carbonyl compounds. Optimum reaction conditions have also been defined to obtain alcohols exclusively by reduction of oxathiolanes. Reactions are rapid at room temperature and do not require protection from atmosphere. Mild reaction conditions, simple work up, and high yields are some of the major advantages of the procedure.
A Mild and Efficient Oxidation of Alcohols to Ketones with Iodosobenzene/(Salen) Manganese Complex
Kim, Sung Soo,Borisova, Galina
, p. 3961 - 3967 (2003)
An excellent method for the chemoselective oxidation of alcohols to ketones with C6H5IO catalyzed by (salen) manganese/4A MS in CH3CN has been devised. The reported procedure is fast, simple, and the yields are excellent (> 95%) in most cases.
An efficient and practical aerobic oxidation of benzylic methylenes by recyclable: N -hydroxyimide
Wang, Jian,Zhang, Cheng,Ye, Xiao-Qing,Du, Wenting,Zeng, Shenxin,Xu, Jian-Hong,Yin, Hong
, p. 3003 - 3011 (2021)
An efficient and practical benzylic aerobic oxidation catalyzed by cheap and simple N-hydroxyimide organocatalyst has been achieved with high yields and broad substrate scope. The organocatalyst used can be recycled and reused by simple workup and only minute amount (1 mol% in most cases) of simple iron salt is used as promoter. Phenyl substrates with mild and strong electron-withdrawing group could also be oxygenated in high yields as well as other benzylic methylenes. Influence of substituents, gram-scale application, catalysts decay and general mechanism of this methodology has also been discussed. This journal is
TEMPO-tert-butyl nitrite: An efficient catalytic system for aerobic oxidation of alcohols
He, Xijun,Shen, Zhenlu,Mo, Weimin,Sun, Nan,Hu, Baoxiang,Hu, Xinquan
, p. 89 - 92 (2009)
A metal-free catalytic system consisting of 2,2,6,6-tetramethylpiperidine N-oxyl (TEMPO) and tert-butyl nitrite has been developed to activate molecular oxygen for the aerobic oxidation of alcohols. A variety of active and non-active alcohols were oxidized to their corresponding carbonyl compounds in high selectivity and yields.
Stereoselective oxidation and reduction by immobilized Geotrichum candidum in an organic solvent
Nakamura, Kaoru,Inoue, Yuko,Matsuda, Tomoko,Misawa, Ibuki
, p. 2397 - 2402 (1999)
Cells of the fungus, Geotrichwn candidum, were immobilized on a water-absorbing polymer and used for stereoselective oxidation and reduction in an organic solvent using cyclohexanone, cyclopentanol or alkan-2-ols as additive. Enantiomerically pure (.β)-1-arylethanols were obtained by the stereoselective oxidation of racemic 1-arylethanols, whereas enantiomerically pure (S)- 1-arylethanols were obtained by the reduction of the corresponding ketones, in contrast to reduction in water by the free cells in which (R)- or (S)- 1-arylethanols were produced in low ee. The reaction mechanism was investigated by measuring the partition of the substrates and products between the organic phase and aqueous phase in the polymer around which the cells were immobilized. Deuterated compounds were used to determine the role of the additives.
Enantiocomplementary C–H Bond Hydroxylation Combining Photo-Catalysis and Whole-Cell Biocatalysis in a One-Pot Cascade Process
Peng, Yongzhen,Li, Danyang,Fan, Jiajie,Xu, Weihua,Xu, Jian,Yu, Huilei,Lin, Xianfu,Wu, Qi
, p. 821 - 825 (2020)
Enantiocomplementary hydroxylation of alkyl aromatics through a one-pot photo-biocatalytic cascade reaction is described. The photoredox process is implemented in aqueous phase with O2 as oxidant and the subsequent (R)- or (S)-selective bioreduction is performed by whole cell system without the addition of the expensive cofactor (NADPH). This mild, operationally simple protocol transforms a wide variety of readily available aromatic compounds into valuable chiral alcohols with high yield (up to 90 %) and stereoselectivity (up to 99 %), thereby displaying important potentials in organic synthesis.
Catalytic Friedel-Crafts acylation of alkoxybenzenes mediated by aluminum hydrogensulfate in solution and solvent-free conditions
Salehi, Peyman,Khodaei, Mohammad Mehdi,Zolfigol, Mohammad Ali,Sirouszadeh, Sara
, p. 1863 - 1864 (2003)
Friedel-Crafts acylation of alkoxybenzenes was achieved efficiently by a reaction with aliphatic acid anhydrides in the presence of catalytic amounts of aluminum hydrogensulfate, Al(HSO4)3, in nitromethane and under solvent-free conditions. Alkylbenzenes and aryl halides, as well as aromatic anhydrides, remained intact under these conditions.
Liquid-phase oxidation of 1-isopropyl- and 1-ethyl-4-methoxybenzenes with oxygen to hydroperoxides
Zawadiak, Jan,Stec, Zbigniew,Jakubowski, Bartlomiej,Orlinska, Beata
, p. 89 - 94 (2003)
A study was carried out on the kinetics of free-radical chain oxidation of 1-isopropyl-4-methoxybenzene (1a) and 1-ethyl-4-methoxybenzene (1b) with oxygen in the liquid phase to yield 1-methyl-1-(4-methoxyphenyl)ethyl hydroperoxide (2a) and 1-(4-methoxyphenyl)ethyl hydroperoxide (2b). The oxidizability of 1a and 1b was studied over the temperature range 50-100°C. Long-term oxidations of 1a and 1b to the corresponding hydroperoxides were carried out and the properties and thermal stability of 2a were established.
