Copper-Catalyzed Oxidative Cleavage of Electron-Rich Olefins in Water at Room Temperature

Lippincott, Daniel J.; Trejo-Soto, Pedro Josué; Gallou, Fabrice; Lipshutz, Bruce H.

doi:10.1021/acs.orglett.8b01883

Cited by 40 publications

(11 citation statements)

References 31 publications

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“…Alternatively, constructions of homemade ozone generators were reported in the past but have not been widely utilized due to several drawbacks such as low ozone production rate (15–30 mg/h), [12] the safety issues concerning high voltages (15–20 kVolts), [13] and elaborate equipment setup [14] . On the other hand, many research groups attempted to seek alternatives to ozonolysis for oxidative cleavages with oxidizing agents such as meta ‐chloroperoxybenzoic acid ( m ‐CPBA), [15] Oxone®, [9a] PhIO/HBF 4 , [16] Fe(OTf) 3 /PyBisulidine/O 2 , [9b] Pd(OAc) 2 /O 2 , [17] Cu 2 (OH) 2 CO 3 /TBHP, [9c] H 2 WO 4 /H 2 O 2 , [18] and OsO 4 /NaIO 4 [19] . Some of these methods still suffered from harsh conditions, low yields, and production of toxic metal wastes.…”

Section: Introductionmentioning

confidence: 99%

Household Ozone Disinfector as An Alternative Ozone Generator for Ozonolysis of Alkenes

et al. 2021

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Ozonolysis is an oxidative cleavage reaction of alkenes with ozone that is indispensable and has found many applications in organic synthesis. However, dedicated laboratory ozone generators are quite expensive equipment and may not be affordable by many laboratories. Recently, lowcost ozone disinfectors have become more common as a household appliance. Herein, we demonstrate the applicability of a household ozone disinfector, which can produce ozone in the order of 10 mmol/h, as alternative equipment for the laboratory scale ozonolysis of alkenes. The ozonolysis of 14 styrene derivatives bearing electron-donating and electron-withdrawing groups on aromatic rings including those with αand β-substituents, as well as 8 natural products containing olefinic moieties were investigated. Ozonolysis of these alkenes at millimole scales proceeded to completion within 30-40 minutes and the carbonyl products were obtained in 68% to quantitative yields. Preparative-scale ozonolysis of 4-methoxystyrene (6.17 g, 46 mmol) was also demonstrated. The reaction proceeded smoothly to yield 4anisaldehyde in 92% yield, which was subsequently converted to p-anisaldehyde dimethyl acetal in 66% yield. This work presents household ozone disinfector as an affordable, compact size, and practical synthetic equipment that does not require extra modification. Thus, the household ozone disinfector offers convenient access to ozonolysis or other reactions involving ozone for low-budget laboratories.

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Section: Introductionmentioning

confidence: 99%

Household Ozone Disinfector as An Alternative Ozone Generator for Ozonolysis of Alkenes

et al. 2021

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“…Enol ethers 1a – 1t are known compounds except 1c and are prepared by following the literature report. − …”

Section: Methodsmentioning

confidence: 99%

Direct α-Benzylation of Methyl Enol Ethers with Activated Benzyl Alcohols: Its Rearrangement and Access to (±)-Tetrahydronyasol, Propterol A, and 1,3-Diarylpropane

Jena

Khan

2019

J. Org. Chem.

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Herein, we report a one-pot Lewis acid mediated synthesis of bi-and triarylpropanal derivatives and their corresponding isomeric ketones from aromatic enol ethers. This transformation takes place via nucleophilic attack of enol ethers to electron-rich benzyl alcohols. The substrate scope of this indicates that it might proceed via quinomethoxy methide as a key intermediate leading to propanal derivatives, and their Wagner−Meerwein rearrangement afforded isomeric ketones. Further, this methodology was applied for the synthesis of (±)-tetrahydronyasol, propterol A, and 1,3diarylpropane.

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“…Molecular oxygen used as an oxidant and this strategy is carried out smoothly under mild conditions with several substrates (Scheme 14A) [28] . Similarly, Lipshutz and co‐workers described an oxidative cleavage of enol ethers into their corresponding ketones using Cu‐catalyzed at room temperature under an aqueous medium which highlights the safe and green features of this methodology (Scheme 14B) [29,30] …”

Section: Reactions Of Alkyl Enol Ethersmentioning

confidence: 99%

Alkyl Enol Ethers: Development in Intermolecular Organic Transformation

Ahmad

Jena

Khan

2021

Chemistry An Asian Journal

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Alkyl enol ethers (AEE) are versatile synthetic intermediates with a unique reactivity pattern. This review article summarizes the synthesis of AEE as well as its reactivity and how enol ether undergoes intermolecular reactions for various bond formation, leading to the construction of several useful organic molecules. The synthetic applications of alkyl enol ethers towards intermolecular bond‐forming reactions include metal‐catalyzed reactions, cycloaddition and heterocycle formation as well as rwactions in the field of natural products synthesis. The achievement of these impressive transformations prove the countless synthetic potential of AEE. The main objective of this review is to bring attentiveness among synthetic chemists to show how AEE extensively can be used to react with both electrophiles as well as nucleophiles, thereby behaving as an ambiphilic reactant. We trust that the unique reactivity pattern of alkyl enol ethers and the fundamental mechanistic idea can attract chemists in AEE chemistry. Exclusively, intermolecular reactions of AEE with other functionalized moieties have not been reviewed to the best of our knowledge.

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Copper-Catalyzed Oxidative Cleavage of Electron-Rich Olefins in Water at Room Temperature

Cited by 40 publications

References 31 publications

Household Ozone Disinfector as An Alternative Ozone Generator for Ozonolysis of Alkenes

Household Ozone Disinfector as An Alternative Ozone Generator for Ozonolysis of Alkenes

Direct α-Benzylation of Methyl Enol Ethers with Activated Benzyl Alcohols: Its Rearrangement and Access to (±)-Tetrahydronyasol, Propterol A, and 1,3-Diarylpropane

Alkyl Enol Ethers: Development in Intermolecular Organic Transformation

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