Oxidation of organosulfur compounds promoted by continuous-flow chemistry

Colomer, Juan P.; Traverssi, Miqueas G.; Oksdath‐Mansilla, Gabriela

doi:10.1007/s41981-019-00066-5

Cited by 16 publications

(10 citation statements)

References 40 publications

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“…Scheme 1 Chemical transformations of the thiocyanate group environmentally harmless organic dyes [12,13], heterogeneous photo-catalysts [14,15], or electrochemical procedures (Scheme 2) [16][17][18]. Nowadays, the implementation of the continuous-flow technology appears as chemoselective, safer and greener procedure for the synthesis of organosulfur compounds, which can be easily scaled up to a gram scale [19]. In addition, photochemical transformations can similarly benefit in improved yields, decreased reaction time-scales, and reduced catalyst loadings due to the highly efficient irradiation that result from having a short path length [20,21].…”

Section: R-s-cfmentioning

confidence: 99%

Photochemical Csp2–H bond thiocyanation and selenocyanation of activated arenes, batch and continuous-flow approaches

Lemir

Oksdath‐Mansilla

Castro‐Godoy

et al. 2022

Photochem Photobiol Sci

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Herein, we report an eco-friendly photochemical oxidative C sp 2 -H thiocyanation and selenocyanation of activated arenes. The reaction proceeds under Violet LED irradiation in the presence of K 2 S 2 O 8 , which quickly oxidizes KSCN and KSeCN, finally producing arylthio/selenocyanates. Using this benign, atom-economic protocol, the desired chalcogenide products were obtained regioselectively, with isolated yields that range from very good to excellent. Although, mechanistic study indicates that it is difficult to distinguish between a radical to a S E Ar reaction mechanism between the photo-induced formed • SCN, for the former, or NCSSCN, for the latter, to the aromatic heterocycles. The inhibition experiment together with the observed reactivity and regioselectivity, would be in agreement with the latter. The synthetic methodology designed could be successfully adapted to continuous-flow systems in a segmented-flow regime, employing the organic phase as the product reservoir. Using this setup, the advantage of the latter can be demonstrated by reducing the reaction time and improving the product yields. Similarly, the scaling up of the reaction to gram scale resulted in favorable outcomes by the flow setup, which installs the photo-flow chemistry as a powerful tool to be included into routine reaction procedures, which have great relevance for the pharmaceutical industry.

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Section: R-s-cfmentioning

confidence: 99%

Photochemical Csp2–H bond thiocyanation and selenocyanation of activated arenes, batch and continuous-flow approaches

Lemir

Oksdath‐Mansilla

Castro‐Godoy

et al. 2022

Photochem Photobiol Sci

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Section: Oxidation and Related Transformationsmentioning

confidence: 99%

“…However, due to their propensity for overoxidation, exact control of the reaction time and oxidant stoichiometry is of paramount importance to avoid sulfone formation, hence flow chemistry has been evaluated as a processing solution. While pursuing this work, a review on this subject has also been published by Colomer and co-workers [ 365 ]. In this area Doherty et al have published widely on the application of peroxotungstates being immobilised on ionic resins that allow for selective oxidisation along with a low catalyst leaching.…”

Section: Reviewmentioning

confidence: 99%

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

Gambacorta¹,

Sharley²,

Baxendale³

2021

Beilstein J. Org. Chem.

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Due to their intrinsic physical properties, which includes being able to perform as volatile liquids at room and biological temperatures, fragrance ingredients/intermediates make ideal candidates for continuous-flow manufacturing. This review highlights the potential crossover between a multibillion dollar industry and the flourishing sub-field of flow chemistry evolving within the discipline of organic synthesis. This is illustrated through selected examples of industrially important transformations specific to the fragrances and flavours industry and by highlighting the advantages of conducting these transformations by using a flow approach. This review is designed to be a compendium of techniques and apparatus already published in the chemical and engineering literature which would constitute a known solution or inspiration for commonly encountered procedures in the manufacture of fragrance and flavour chemicals.

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“…13−15 Continuous processes have been investigated as well. 16 Despite these developments in organosulfur oxidation processes, most lack industrial interest, owing to sustainability, scaling-up, and safety concerns.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Many variations of the organosulfur oxidation process have been developed to generate more viable and long-lasting oxidative procedures that will have an impact on the pharmaceutical industry to reduce cost, waste, and byproducts. Generally, such oxidation processes can be performed using different oxidants such as peroxides, , photocatalytic processes, , or hypervalent iodine reagents. − Continuous processes have been investigated as well . Despite these developments in organosulfur oxidation processes, most lack industrial interest, owing to sustainability, scaling-up, and safety concerns.…”

Section: Introductionmentioning

confidence: 99%

Flow Electrosynthesis of Sulfoxides, Sulfones, and Sulfoximines without Supporting Electrolytes

Amri

Wirth

2021

J. Org. Chem.

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An efficient electrochemical flow process for the selective oxidation of sulfides to sulfoxides and sulfones and of sulfoxides to N-cyanosulfoximines has been developed. In total, 69 examples of sulfoxides, sulfones, and N-cyanosulfoximines have been synthesized in good to excellent yields and with high current efficiencies. The synthesis was assisted and facilitated through a supporting electrolyte-free, fully automated electrochemical protocol that highlights the advantages of flow electrolysis.

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Oxidation of organosulfur compounds promoted by continuous-flow chemistry

Cited by 16 publications

References 40 publications

Photochemical Csp2–H bond thiocyanation and selenocyanation of activated arenes, batch and continuous-flow approaches

Photochemical Csp2–H bond thiocyanation and selenocyanation of activated arenes, batch and continuous-flow approaches

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

Flow Electrosynthesis of Sulfoxides, Sulfones, and Sulfoximines without Supporting Electrolytes

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