Versatile Electrochemical Oxidative C(sp2)−H Bond Selenylation of Resveratrol

A simple and environmentally benign procedure for electrochemical oxidative mono‐ and bis‐selenylation of the resveratrol C(sp2)−H bond was developed. Driven by galvanostatic electrolysis in an undivided cell, it provided efficient transformation under oxidant‐, base‐, and transition metal‐free cond...

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Bibliographic Details
Published in:European journal of organic chemistry 2021-08, Vol.2021 (31), p.4411-4416
Main Authors: Lazzaris, Maika J., Martins, Guilherme M., Xavier, Fernando R., Braga, Antonio L., Mendes, Samuel R.
Format: Article
Language:English
Subjects:
C−H bond functionalization
Electrolysis
Electrosynthesis
Functional groups
Hydrogen bonds
Open systems
Organochalcogen
Oxidizing agents
Resveratrol
Room temperature
Selenylation
Transition metals
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Summary:A simple and environmentally benign procedure for electrochemical oxidative mono‐ and bis‐selenylation of the resveratrol C(sp2)−H bond was developed. Driven by galvanostatic electrolysis in an undivided cell, it provided efficient transformation under oxidant‐, base‐, and transition metal‐free conditions, in an open system at room temperature. With satisfactory functional group compatibility, it required a substoichiometric amount of NaI, which acted as an electrolyte and mediator. The work describes an electrochemical oxidative C(sp2)−H selenylation of resveratrol. Driven by galvanostatic electrolysis in an undivided cell, it provided efficient transformation in an open system at room temperature. Using this benign, atom‐economic protocol, the desired selenylated products were obtained regioselectively, in good to excellent yields by using half molar equiv. of the diselenides.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202100568