Combining engineering and chemistry for the selective continuous production of four different oxygenated compounds by photo-oxidation of cyclopentadiene using liquid and supercritical CO2 as solvents

Wu, Lingqiao; Abada, Zahra; Lee, Darren S.; Poliakoff, Martyn; George, Michael W.

doi:10.1016/j.tet.2017.11.048

Cited by 13 publications

(18 citation statements)

References 49 publications

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“…The high pressure equipment used in this study has been described previously. [20] Such equipment should be used with caution and only with the appropriate safety measures in place. A simplified diagram of the setup is shown in Figure 1.…”

Section: Resultsmentioning

confidence: 99%

“…[28,29] Our starting conditions were those which we reported for the photooxidation of cyclopentadiene. [20] The CO2-soluble photosensitizer TPFPP (5,10,15,20-tetrakis-(pentafluorophenyl)porphyrin) was chosen as the catalyst for the reaction as this has been successfully employed in our system before. [18] As 1a is quite a viscous oil, a co-solvent was used so that the mixture could be pumped with minimal blockages; initially methanol was chosen.…”

Section: Resultsmentioning

confidence: 99%

“…Recently, we reported the photo-oxidation of cyclopentadiene using liqCO2 and scCO2 in a pressurized continuous flow system. [20] The endoperoxide formed in this reaction is unstable and can be difficult to handle in large quantities. Therefore, we used liqCO2 and scCO2 to produce a modular engineering approach with different quench reagents that could be fed in downstream of the photoreactor, allowing access to a choice of four different compounds.…”

Section: Introductionmentioning

confidence: 99%

“…Simplified schematic of the high pressure continuous flow setup [20]. CO2 is delivered from a chilled CO2 pump and O2 is dosed at a known rate via a Rheodyne dosage unit.…”

mentioning

confidence: 99%

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Photooxidation of Fulvenes in a Continuous Flow Photoreactor using Carbon Dioxide as a Solvent

Lee

Boufroura

et al. 2018

ChemPhotoChem

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A range of 3-substituted oxepinones have been synthesised by the photo-oxidation of fulvenes with photochemically generated singlet oxygen (1 O2) using carbon dioxide (CO2) as a solvent and a CO2-soluble porphyrin photosensitizer. The reactive intermediates generated in this reaction decompose to yield a range of useful and underutilized building blocks that are not easily accessible using more traditional reaction setups. Fulvenes containing an exocyclic allylic hydrogen are shown to form three products via potentially competing intramolecular pathways, which can be tuned to some extent by adjusting the conditions in the flow reactor. A range of substrates containing a variety of functional groups was examined; this led to lower yields of the desired lactones being observed in the case of compounds containing polar electron-donating groups. We also demonstrate that one of the lactones can be further hydrogenated over a Pd/C catalyst to the unsaturated 7-membered ring in high yield.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…Simplified schematic of the high pressure continuous flow setup [20]. CO2 is delivered from a chilled CO2 pump and O2 is dosed at a known rate via a Rheodyne dosage unit.…”

mentioning

confidence: 99%

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Photooxidation of Fulvenes in a Continuous Flow Photoreactor using Carbon Dioxide as a Solvent

Lee

Boufroura

et al. 2018

ChemPhotoChem

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“…Oliveira and co‐workers developed a continuous flow photooxygenation of conjugated dienes to yield endoperoxides hydroxyenones, substituted furans, and 1,4‐dicarbonyl derivatives after an in situ transformation of the endoperoxide (Scheme ) . Furthermore, Poliakoff, George and co‐workers produced a range of different products derived from the photooxygenation of pentadiene using either liquid or supercritical CO 2 as solvent …”

Section: ‐Membered Ringsmentioning

confidence: 99%

Flow Chemistry for Cycloaddition Reactions

2020

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Continuous flow reactors form part of a rapidly growing research area that has changed the way synthetic chemistry is performed not only in academia but also at the industrial level. This Review highlights the most recent advances in cycloaddition reactions performed in flow systems. Cycloadditions are atom-efficient transformations for the synthesis of carbo-and heterocycles, involved in the construction of challenging skeletons of complex molecules. The main advantages of translating these processes into flow include using intensified conditions, safer handling of hazardous reagents and gases, easy tuning of reaction conditions, and straightforward scaling up. These benefits are especially important in cycloadditions such as the copper(I)-catalyzed azide alkyne cycloaddition (CuAAC), Diels-Alder reaction, ozonolysis and [2 + 2] photocycloadditions. Some of these transformations are key reactions in the industrial synthesis of pharmaceuticals.

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On-line SFC-UV/Vis-MS using flow selection interfaces to monitor continuous flow single and sequential stage organic reactions in supercritical carbon dioxide

Guo¹,

Li²,

Chi³

et al. 2023

The Journal of Supercritical Fluids

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Combining engineering and chemistry for the selective continuous production of four different oxygenated compounds by photo-oxidation of cyclopentadiene using liquid and supercritical CO2 as solvents

Cited by 13 publications

References 49 publications

Photooxidation of Fulvenes in a Continuous Flow Photoreactor using Carbon Dioxide as a Solvent

Photooxidation of Fulvenes in a Continuous Flow Photoreactor using Carbon Dioxide as a Solvent

Flow Chemistry for Cycloaddition Reactions

On-line SFC-UV/Vis-MS using flow selection interfaces to monitor continuous flow single and sequential stage organic reactions in supercritical carbon dioxide

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