Electrochemical bromofunctionalization of alkenes in a flow reactor

Seitz, Jakob; Wirth, Thomas

doi:10.1039/d1ob01302e

Cited by 12 publications

(14 citation statements)

References 33 publications

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“…[39,[42][43] The electrochemical bromofunctionalization of alkenes including the generation of 1,2-vicinal dihalides have attracted special attention. [44][45][46][47][48][49][50] Many great protocols have been reported recently for the electrochemical bromination of alkenes featuring direct electrochemical bromination, [44][45] electrocatalytic bromination [48] and bromination via linear paired electrosynthesis. [46,49] Recently, the electrochemical bromofunctionalization of alkenes in a flow reactor was also reported.…”

Section: Introductionmentioning

confidence: 99%

“…[47] While these methods are widely applicable and provide good to excellent yields, they often utilize dangerous bromine sources, such as HBr, [45,47] and depleting metal electrodes. [44][45][46][47][48] To overcome these drawbacks, a novel method for the transhalogenation of numerous alkenes via an electron shuttle reaction was recently reported by our group. [49] Nevertheless, while the electrochemical bromination of simple alkenes was extensively researched, the functionalization of naturally derived compounds and especially the dibromination of terpenes and terpenoids casts only very few examples.…”

Section: Introductionmentioning

confidence: 99%

“…[46,49] Recently, the electrochemical bromofunctionalization of alkenes in a flow reactor was also reported. [47] While these methods are widely applicable and provide good to excellent yields, they often utilize dangerous bromine sources, such as HBr, [45,47] and depleting metal electrodes. [44][45][46][47][48] To overcome these drawbacks, a novel method for the transhalogenation of numerous alkenes via an electron shuttle reaction was recently reported by our group.…”

Section: Introductionmentioning

confidence: 99%

“…Furthermore, constant current conditions in combination with carbon‐based electrodes allow an easy and safe operation by simply switching on or off the electrochemical current [39,42–43] . The electrochemical bromofunctionalization of alkenes including the generation of 1,2‐vicinal dihalides have attracted special attention [44–50] . Many great protocols have been reported recently for the electrochemical bromination of alkenes featuring direct electrochemical bromination, [44–45] electrocatalytic bromination [48] and bromination via linear paired electrosynthesis [46,49] .…”

Section: Introductionmentioning

confidence: 99%

“…Many great protocols have been reported recently for the electrochemical bromination of alkenes featuring direct electrochemical bromination, [44–45] electrocatalytic bromination [48] and bromination via linear paired electrosynthesis [46,49] . Recently, the electrochemical bromofunctionalization of alkenes in a flow reactor was also reported [47] . While these methods are widely applicable and provide good to excellent yields, they often utilize dangerous bromine sources, such as HBr, [45,47] and depleting metal electrodes [44–48] .…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Selective Electrochemical Dibromination of Terpenes and Naturally Derived Olefins

et al. 2022

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A simple electrochemical protocol is established for the selective alkene dibromination of naturally derived olefins, such as terpenes. The use of hazardous Br 2 or its analogues have been elegantly avoided by employing readily available, inexpensive, and harmless sodium bromide with a dual role as reagent and supporting electrolyte in combination with sustainable carbon-based electrodes. This electrochemical protocol provides the desired products with good to excellent yields up to 82 % with 10 examples. Scalability has been proved by a 5fold scale-up. Notably, higher yields and selectivity were achieved in comparison to conventional bromination by Br 2 and DMSO/HBr system and the dibrominated compound was eligible for further functionalization, such as cyanation according to the Kolbe nitrile synthesis protocol.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Selective Electrochemical Dibromination of Terpenes and Naturally Derived Olefins

et al. 2022

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Synthesis of Enantiopure Vicinal Halohydrins Using a Sequence of Haloperoxidase and Lipase

De Marchi,

Hilberath,

Zippilli

et al. 2024

Adv Synth Catal

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Vicinal halohydrins are key building blocks to produce bioactive molecules and drugs, especially if they can be obtained in enantiomerically pure form. In this study, we present a bi‐enzymatic sequence that allows to obtain vic‐halohydrins through a photochemoenzymatic olefin hydroxy halogenation followed by a lipase catalysed kinetic resolution. The absolute configuration of the resulting products was determined using Mosher’s method.

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Electro‐Oxidation of Alkenes: A Green Approach Towards Functionalized Oxygenates

Sun,

Hu,

2024

ChemCatChem

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In chemical industrial process, conversion of alkenes to functional oxygenates plays a key role in bridging between the feedstock and downstream application. Traditionally, the oxidation required highly‐active oxygen sources or molecular oxygen under high temperature and pressure. This poses challenges to the green and safe production of oxygenates. To circumvent the issues of massive consumption of fossil fuel and serious CO2 footprints, approaches of electro‐oxidation are developed under ambient conditions, adopting O2 and H2O as oxygen source. Utilizing electricity from renewable resources and the involved electron transfer, the performance is closely related to the interface characteristics of electrodes and electrolytes. This review presents the progress in catalysts design, electrolytes optimization, cells integration to effectively regulate the microenvironment of the interfaces. Further discussion of the mechanism analysis and potential issues are emphasized, based on the in‐situ characterization techniques, isotopic experiments and quenching tests. We hope this review can provide an outline for green approaches to oxidation of alkenes via electrocatalytic pathways.

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Electrochemical bromofunctionalization of alkenes in a flow reactor

Abstract: The bromination of organic molecules has been extensively studied to date, yet there is still a demand for safe and sustainable methodologies. Hazardous reagents, selectivity, low atom economy and waste...

Cited by 12 publications

References 33 publications

Selective Electrochemical Dibromination of Terpenes and Naturally Derived Olefins

Selective Electrochemical Dibromination of Terpenes and Naturally Derived Olefins

Synthesis of Enantiopure Vicinal Halohydrins Using a Sequence of Haloperoxidase and Lipase

Electro‐Oxidation of Alkenes: A Green Approach Towards Functionalized Oxygenates

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