Selective Oxidation of Sulfides in Flow Chemistry

Silva, Filipa; Baker, Alastair; Stansall, James; Michalska, Weronika; Yusubov, M. S.; Graz, Michael; Saunders, Robert M.; Evans, Gareth J. S.; Wirth, Thomas

doi:10.1002/ejoc.201800339

Cited by 29 publications

(13 citation statements)

References 23 publications

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“…With the optimal reaction conditions determined, we first evaluated the scope of the electrochemical fluorosulfenylation of alkenes (Table 2). This reaction accommodated a wide array of para-, meta-, and orthosubstituted styrenes (5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17). Additionally, alkyl (18)(19)(20)(21), benzyl (22), pyridyl (23), and cycloalkyl (24-27) αsubstituted styrenes were all found to be well tolerated.…”

Section: Substrate Scopementioning

confidence: 90%

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Electrochemistry Enabled Selective Vicinal Fluorosulfenylation and Fluorosulfoxidation of Alkenes

Jiang

et al. 2021

Preprint

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Both sulfur and fluorine play important roles in organic synthesis, the life science, and materials science. The direct incorporation of these elements into organic scaffolds with precise control of the oxidation states of sulfur moieties is of great significance. Herein, we report the highly selective electrochemical vicinal fluorosulfenylation and fluorosulfoxidation reactions of alkenes, which were enabled by the unique ability of electrochemistry to dial in the potentials on demand. Preliminary mechanistic investigations revealed that the fluorosulfenylation reaction proceeded through a radical-polar crossover mechanism involving a key episulfonium ion intermediate. Subsequent electrochemical oxidation of fluorosulfides to fluorosulfoxides were readily achieved under a higher applied potential with the adventitious H2O in the reaction mixture.

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Section: Substrate Scopementioning

confidence: 90%

“…Therefore, it is highly desirable to develop synthesis protocols to simultaneously introduce sulfur and fluorine elements into targeted molecules with precise control of the oxidation states of the sulfur moieties. [8][9][10]…”

Section: Introductionmentioning

confidence: 99%

Electrochemistry Enabled Selective Vicinal Fluorosulfenylation and Fluorosulfoxidation of Alkenes

Jiang

et al. 2021

Preprint

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“…The application in flow enabled a lower catalyst loading and reduced residence times (Scheme 94) [366,367]. Along with the sulfoxides, thiosulfinates have been synthesised in flow using a packed-bed reactor filled with oxone as described by Wirth et al (Scheme 95) [368]. This approach has been used to prepare very reactive metabolic sulfoxides and sulfenic acids present in garlic at increased scale.…”

Section: Oxidation and Related Transformationsmentioning

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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“…% of CF 3 COOH were fluxed in a packed-bed reactor filled with Oxone ®® . In the latter case, an example of selective mono-oxygenation of a disulfide was also described [28].…”

Section: Introductionmentioning

confidence: 99%

Continuous Bioinspired Oxidation of Sulfides

et al. 2020

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A simple, efficient, and selective oxidation under flow conditions of sulfides into their corresponding sulfoxides and sulfones is reported herein, using as a catalyst perselenic acid generated in situ by the oxidation of selenium (IV) oxide in a diluted aqueous solution of hydrogen peroxide as the final oxidant. The scope of the proposed methodology was investigated using aryl alkyl sulfides, aryl vinyl sulfides, and dialkyl sulfides as substrates, evidencing, in general, a good applicability. The scaled-up synthesis of (methylsulfonyl)benzene was also demonstrated, leading to its gram-scale preparation.

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Selective Oxidation of Sulfides in Flow Chemistry

Abstract: A packed‐bed reactor with oxone has been employed for selective oxidations of sulfur compounds. Various sulfides containing different functional groups are efficiently oxidized to the corresponding sulfoxides without formation of sulfones or other side products.

Cited by 29 publications

References 23 publications

Electrochemistry Enabled Selective Vicinal Fluorosulfenylation and Fluorosulfoxidation of Alkenes

Electrochemistry Enabled Selective Vicinal Fluorosulfenylation and Fluorosulfoxidation of Alkenes

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

Continuous Bioinspired Oxidation of Sulfides

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