Silver Carbonate on Celite Oxidations

Fétizon, M.; Golfier, M.; Mourgues, P.; Louis, Jean-Marie

doi:10.1007/978-1-4613-2109-5_10

Cited by 8 publications

(3 citation statements)

References 202 publications

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“…The selective oxidation of alcohols to the corresponding carbonyl compounds is a frequently used transformation in organic synthesis, and hence a wide variety of methods has been developed. Swern oxidation, Dess−Martin oxidation, and various metal reagents are employed for this purpose. Unfortunately, these oxidations call for the use of at least a stoichiometric amount of oxidants and bring about a large quantity of noxious byproducts.…”

Section: Introductionmentioning

confidence: 99%

Efficient Oxidation of Alcohols to Carbonyl Compounds with Molecular Oxygen Catalyzed by N-Hydroxyphthalimide Combined with a Co Species

et al. 2000

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Highly efficient catalytic oxidation of alcohols with molecular oxygen by N-hydroxyphthalimide (NHPI) combined with a Co species was developed. The oxidation of 2-octanol in the presence of catalytic amounts of NHPI and Co(OAc)2 under atmospheric dioxygen in AcOEt at 70 degrees C gave 2-octanone in 93% yield. The oxidation was significantly enhanced by adding a small amount of benzoic acid to proceed smoothly even at room temperature. Primary alcohols were oxidized by NHPI in the absence of any metal catalyst to form the corresponding carboxylic acids in good yields. In the oxidation of terminal vic-diols such as 1,2-butanediol, carbon-carbon bond cleavage was induced to give one carbon less carboxylic acids such as propionic acid, while internal vic-diols were selectively oxidized to 1,2-diketones.

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Section: Introductionmentioning

confidence: 99%

Efficient Oxidation of Alcohols to Carbonyl Compounds with Molecular Oxygen Catalyzed by N-Hydroxyphthalimide Combined with a Co Species

et al. 2000

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“…This method is used to oxidize primary alcohols to aldehydes, which form intramolecular semiacetals (cyclization with tertiary OH group) that are quickly oxidized to lactones. 9 After several runs, we observed significant batch-to-batch variations in reaction time and yield. We then turned to the TEMPO/PIDA 10 catalytic system.…”

Section: Resultsmentioning

confidence: 89%

“…To that end, we first attempted reacting 8 with silver carbonate on Celite. This method is used to oxidize primary alcohols to aldehydes, which form intramolecular semiacetals (cyclization with tertiary OH group) that are quickly oxidized to lactones . After several runs, we observed significant batch-to-batch variations in reaction time and yield.…”

Section: Resultsmentioning

confidence: 94%

Total Synthesis of Penicyclone A Using a Double Grignard Reaction

et al. 2022

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We describe the first total synthesis of penicyclone A, a novel deep-sea fungus-derived polyketide, and a reevaluation of its antimicrobial activity. The synthesis of this unique spirolactone was achieved in 10 steps starting from a known D-ribose derivative. The key steps include a double Grignard reaction for the diastereoselective construction of the chiral tertiary alcohol intermediate, tandem oxidation/cyclization, and photooxygenation, followed by an oxidative rearrangement to introduce the enone functionality.

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Celite

Heidelbaugh¹

2001

Encyclopedia of Reagents for Organic Synthesis

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Silver Carbonate on Celite Oxidations

Cited by 8 publications

References 202 publications

Efficient Oxidation of Alcohols to Carbonyl Compounds with Molecular Oxygen Catalyzed by N-Hydroxyphthalimide Combined with a Co Species

Efficient Oxidation of Alcohols to Carbonyl Compounds with Molecular Oxygen Catalyzed by N-Hydroxyphthalimide Combined with a Co Species

Total Synthesis of Penicyclone A Using a Double Grignard Reaction

Celite

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