Transition-metal catalyzed oxidation of alcohols to aldehydes and ketones by means of Me3SiOOSiMe3

Kanemoto, Shigekazu; Oshima, Koichiro; Matsubara, Seijiro; Takai, Kazuhiko; Nozaki, Hitosi

doi:10.1016/s0040-4039(00)81878-x

Cited by 81 publications

(12 citation statements)

References 12 publications

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“…[36][37][38] Ruthenium(II) compounds, in conjunction with a variety of oxidants, such as iodosobenzene, methylmorpholine N-oxide, 2,2,6,6-tetramethylpiperidin N-oxyl (TEMPO), bromate, hypochlorite, peroxides, are widely used as the oxidation catalysts. [39][40][41][42][43][44][45][46][47] We have evaluated the catalytic efficacy of compound 2 for alcohol to aldehyde oxidation and aldehyde olefination reactions, and the results are presented in Tables 2 and 3. Treatment of benzylalcohol (1 mmol), TEMPO (2 mmol) and catalyst 2 (0.01 mmol) provided benzaldehyde in 78% yield at 808C after 6 h ( Table 2, entry 1).…”

Section: Resultsmentioning

confidence: 99%

Contrasting Reactivity of 2-Mesityl-1,8-Naphthyridine (Mes-NP) with Singly-Bonded [RhII–RhII] and [RuI–RuI] Compounds

Saha¹,

Rahaman²,

Sinha³

et al. 2011

Aust. J. Chem.

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Reaction of cis-[Rh 2 (CH 3 COO) 2 (CH 3 CN) 6 ](BF 4 ) 2 with two equivalents of 2-mesityl-1,8-naphthyridine (Mes-NP) affords trans-[Rh 2 (CH 3 COO) 2 (Mes-NP) 2 ](BF 4 ) 2 (1). X-ray structure reveals weak Rh-C(ipso) interaction, and a short Rh-Rh distance. The same ligand, in contrast, oxidatively cleaves the Ru-Ru bond in cis-[Ru 2 (CO) 4 (CH 3 CN) 6 ](BF 4 ) 2 and results in trans-[Ru(Mes-NP) 2 (CH 3 CN) 2 ](BF 4 ) 2 (2). Both compounds adopt trans geometry to relieve the steric strain. Compound 2 exhibits moderate activity for the alcohol oxidation and aldehyde olefination reactions.

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Section: Resultsmentioning

confidence: 99%

Contrasting Reactivity of 2-Mesityl-1,8-Naphthyridine (Mes-NP) with Singly-Bonded [RhII–RhII] and [RuI–RuI] Compounds

Saha¹,

Rahaman²,

Sinha³

et al. 2011

Aust. J. Chem.

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“…The PMN-rich cell suspension (cell density: 7 Â 10 3 /ml), mentioned in the PMN method was diluted with HBSS hundred times. Next, the gold sensor chips were exposed to 4,4'-dithiodibutyric acid (2.38 mg) in ethanol (10 ml Although Ru-catalyzed oxidation of chitosan provided a convenient one-pot procedure for the synthesis of oxidized chitosan 3 [33,34], this procedure is not a regioselective oxidation method. We intended to improve the solubility of chitosan derivatives while retaining their advantageous biological properties, such as biocompatibility and biodegradability.…”

Section: Surface Plasmon Resonance Analysis (Spr Method) [26±32]mentioning

confidence: 99%

Regioselective synthesis and biological activity of oxidized chitosan derivatives

Terada¹,

Morimoto

Saimoto

et al. 2003

Polymers for Advanced Techs

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Oxidized chitosan derivatives with various degrees of oxidation (DS, 0.1±1.0) were prepared by the treatment of chitosan with CrO 3 /aq HClO 4 or by the oxidation of 3-O-and N-protected chitosan with 30% aq H 2 O 2 / Na 2 WO 4 followed by 3-O-and N-deprotection. The oxidized products were then N-acetylated with Ac 2 O in order to improve their water-solubility. Although the oxidized chitosan derivative of DS 0.28 and the degree of N-acetylation of chitosan (DA) 38% was insoluble in the pH 3±8 region, that of DS 0.26 and DA 76% was soluble in the neutral pH range. The newly-prepared acetylated and oxidized chitosan derivatives were found to suppress the chemiluminescence response of inflammatory cells such as canine polymorphonuclear cells (PMNs). Analysis by the surface plasmon resonance method revealed that the bind and release behavior of PMNs to acetylated oxidized chitosan derivatives was similar to that against carboxymethylated chitosan derivatives. The amount of water-soluble chitosan derivative bound to cytokine IL-8 was found to be affected by the structural and electronic features of the chitosan substituents in the chitosan chain.

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“…Sodium bromate has been found to be effective for the oxidation of 5 -cholestan-3 -ol 58 to the 3-keto derivative 59 in the presence of cerium(IV) ammonium nitrate as catalyst in 97% yield [159]. The same reaction has also been performed with [160], with pyridinium dichromate-Me 3 SiO OSiMe 3 system [161] and with DMSO catalyzed by a (polystyrene-catecholato)oxorhenium complex (Fig. 13) [162].…”

Section: Mediated By Other Oxidantsmentioning

confidence: 99%

Catalytic Oxidative Processes in Steroid Chemistry: Allylic Oxidation, β-Selective Epoxidation, Alcohol Oxidation and Remote Functionalization Reactions

Salvador¹,

Silvestre²,

Moreira

2006

COC

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The preparation of steroids containing oxygenated functions in suitable positions of the steroid nucleus is of great importance and can be achieved by means of several oxidative processes. In this paper allylic oxidation, -selective epoxidation, alcohol oxidation and remote functionalization reactions in steroid substrates are reviewed. Focus has been given to catalytic processes because of their major importance from the viewpoint of synthetic organic chemistry.

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Transition-metal catalyzed oxidation of alcohols to aldehydes and ketones by means of Me3SiOOSiMe3

Cited by 81 publications

References 12 publications

Contrasting Reactivity of 2-Mesityl-1,8-Naphthyridine (Mes-NP) with Singly-Bonded [RhII–RhII] and [RuI–RuI] Compounds

Contrasting Reactivity of 2-Mesityl-1,8-Naphthyridine (Mes-NP) with Singly-Bonded [RhII–RhII] and [RuI–RuI] Compounds

Regioselective synthesis and biological activity of oxidized chitosan derivatives

Catalytic Oxidative Processes in Steroid Chemistry: Allylic Oxidation, β-Selective Epoxidation, Alcohol Oxidation and Remote Functionalization Reactions

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Transition-metal catalyzed oxidation of alcohols to aldehydes and ketones by means of Me3SiOOSiMe3

Cited by 81 publications

References 12 publications

Contrasting Reactivity of 2-Mesityl-1,8-Naphthyridine (Mes-NP) with Singly-Bonded [RhII–RhII] and [RuI–RuI] Compounds

Contrasting Reactivity of 2-Mesityl-1,8-Naphthyridine (Mes-NP) with Singly-Bonded [RhII–RhII] and [RuI–RuI] Compounds

Regioselective synthesis and biological activity of oxidized chitosan derivatives

Catalytic Oxidative Processes in Steroid Chemistry: Allylic Oxidation, &#946;-Selective Epoxidation, Alcohol Oxidation and Remote Functionalization Reactions

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Catalytic Oxidative Processes in Steroid Chemistry: Allylic Oxidation, β-Selective Epoxidation, Alcohol Oxidation and Remote Functionalization Reactions