6533b82dfe1ef96bd1291ef4
RESEARCH PRODUCT
Electrochemical C−H Functionalization of (Hetero)Arenes—Optimized by DoE
Siegfried R. WaldvogelJohannes L. RöcklDieter SchollmeyerJonas ReinMaurice Dörrsubject
boron-doped diamond540 Chemistry and allied sciencesanodeElectrolyte010402 general chemistryElectrochemistry01 natural sciencesCatalysislaw.inventionC−H functionalizationchemistry.chemical_compoundlawelectrolysisElectrochemistryTriethylaminecaffeineElectrolysis010405 organic chemistryCommunicationArylOrganic ChemistryGeneral ChemistryCombinatorial chemistryCommunications0104 chemical scienceschemistry540 ChemieElectrodeSurface modificationCyclic voltammetrydescription
Abstract A novel approach towards the activation of different arenes and purines including caffeine and theophylline is presented. The simple, safe and scalable electrochemical synthesis of 1,1,1,3,3,3‐hexafluoroisopropanol (HFIP) aryl ethers was conducted using an easy electrolysis setup with boron‐doped diamond (BDD) electrodes. Good yields up to 59 % were achieved. Triethylamine was used as a base as it forms a highly conductive media with HFIP, making additional supporting electrolytes superfluous. The synthesis was optimized using Design of Experiment (DoE) techniques giving a detailed insight to the significance of the reaction parameters. The mechanism was investigated by cyclic voltammetry (CV). Subsequent transition metal‐catalyzed as well as metal‐free functionalization led to interesting motifs in excellent yields up to 94 %.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2020-03-06 | Chemistry – A European Journal |