Hydroxylation of cyclohexane, octan-1-ol, and palmitic acid by trifluoroperoxyacetic acid

Deno, N. C.; Messer, Lauren A.

doi:10.1039/c3976001051a

Cited by 24 publications

(8 citation statements)

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“…It is particularly important that the over-oxidation was suppressed in spite of extremely high conversion. Although trifluoroacetoxylation of hydrocarbons has been reported to occur upon treatment with hydrogen peroxide in trifluoroacetic acid without metal catalyst [12], the reaction is very slow (k = 10 -5 M -1 s -1 ). The second-order rate constant of our ruthenium-catalyzed oxidation of cyclohexane with CH 3 …”

Section: Ruthenium-catalyzed Oxidations Of Alkanes With Tert-butyl Hymentioning

confidence: 99%

Copper complexes for catalytic, aerobic oxidation of hydrocarbons

Murahashi

Komiya

Hayashi

et al. 2001

Pure and Applied Chemistry

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Catalytic oxidation of hydrocarbons can be performed efficiently upon treatment with tert-butylhydroperoxide or peracetic acid in the presence of a low-valent ruthenium catalyst. Furthermore, aerobic oxidation of hydrocarbons can be performed in the presence of acetaldehyde using ruthenium, iron, and copper catalysts. Copper derived from copper chloride/crown ether or copper chloride/crown ether/alkaline metal salts have proved to be efficient catalysts. Further study revealed that specific copper complexes formed from copper salts and acetonitrile are convenient and highly useful catalysts for the aerobic oxidation of unactivated hydrocarbons.Selective oxidation of alkanes is an important topic in view of the economical and ecological use of natural raw materials. However, catalytic oxidation of unactivated hydrocarbons remains as a challenging topic (eq. 1). Direct oxidation of hydrocarbons is one of the important functions of cytochrome P-450. During the course of simulation of the enzymatic functions of cytochrome P-450 with transition-metal complexes, we found that catalytic oxidation of various substrates can be performed highly efficiently [1]. Ruthenium porphyrins bearing meso-pentafluorophenyl group (Ru[TPFPP][CO]) are highly efficient catalysts for aerobic oxidation of alkanes in the presence of acetaldehyde [2]. In contrast, without using porphyrin catalysts, oxidation of alkanes can be performed highly efficiently upon treatment with tert-butylhydroperoxide [3] or peracetic acid [4] in the presence of low-valent ruthenium catalysts. Importantly, aerobic oxidation of alkanes can be performed in the presence of acetaldehyde using ruthenium [5], iron [5], and even copper [6] catalysts. The precise mechanistic study revealed that oxo-metal intermediates are involved in these reactions.The copper complexes derived from copper chloride and crown ethers were found to be extremely efficient catalysts [7,8]. Furthermore, specific copper complexes formed from copper salts and acetonitrile are convenient and highly useful catalysts for the aerobic oxidation of unactivated hydrocarbons [9].

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Section: Ruthenium-catalyzed Oxidations Of Alkanes With Tert-butyl Hymentioning

confidence: 99%

Copper complexes for catalytic, aerobic oxidation of hydrocarbons

Murahashi

Komiya

Hayashi

et al. 2001

Pure and Applied Chemistry

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“…Alkanes are rarely used in the cross-dehydrogenative C–O coupling because of low reactivity of C–H bonds. An example is the trifluoroacetoxylation of cyclohexane, cycloheptane, cyclooctane, and adamantane in trifluoroacetic acid in the presence of peracetic acid [ 296 ] or hydrogen peroxide [ 297 – 299 ] with the addition of transition metal salts (Rh, Ru, Pd, Pt, Fe) [ 296 – 297 ] or in the absence of metal compounds [ 298 – 299 ]; the reactions were usually accomplished at room temperature for a few hours.…”

Section: Reviewmentioning

confidence: 99%

Cross-dehydrogenative coupling for the intermolecular C–O bond formation

Krylov

Vil

Terent’ev

2015

Beilstein J. Org. Chem.

171

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SummaryThe present review summarizes primary publications on the cross-dehydrogenative C–O coupling, with special emphasis on the studies published after 2000. The starting compound, which donates a carbon atom for the formation of a new C–O bond, is called the CH-reagent or the C-reagent, and the compound, an oxygen atom of which is involved in the new bond, is called the OH-reagent or the O-reagent. Alcohols and carboxylic acids are most commonly used as O-reagents; hydroxylamine derivatives, hydroperoxides, and sulfonic acids are employed less often. The cross-dehydrogenative C–O coupling reactions are carried out using different C-reagents, such as compounds containing directing functional groups (amide, heteroaromatic, oxime, and so on) and compounds with activated C–H bonds (aldehydes, alcohols, ketones, ethers, amines, amides, compounds containing the benzyl, allyl, or propargyl moiety). An analysis of the published data showed that the principles at the basis of a particular cross-dehydrogenative C–O coupling reaction are dictated mainly by the nature of the C-reagent. Hence, in the present review the data are classified according to the structures of C-reagents, and, in the second place, according to the type of oxidative systems. Besides the typical cross-dehydrogenative coupling reactions of CH- and OH-reagents, closely related C–H activation processes involving intermolecular C–O bond formation are discussed: acyloxylation reactions with ArI(O2CR)2 reagents and generation of O-reagents in situ from C-reagents (methylarenes, aldehydes, etc.).

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“…394 Further, they have demonstrated that when coal is subjected to trifluoroperacetic acid (CF3COOH) oxidation, benzene polycarboxylic acids are formed only from polyaromatic clusters. [2][3][4] Such a process provides a means both of elucidating the highly informative aliphatic character of coal and also revealing, indirectly, the aromatic structure. The technique also has the advantages of being relatively uncomplicated and rapid.…”

Section: Future Workmentioning

confidence: 99%

Fossil Energy Program. Progress report for October 1979

McNeese¹

1979

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Hydroxylation of cyclohexane, octan-1-ol, and palmitic acid by trifluoroperoxyacetic acid

Cited by 24 publications

References 0 publications

Copper complexes for catalytic, aerobic oxidation of hydrocarbons

Copper complexes for catalytic, aerobic oxidation of hydrocarbons

Cross-dehydrogenative coupling for the intermolecular C–O bond formation

Fossil Energy Program. Progress report for October 1979

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