6533b83afe1ef96bd12a7176
RESEARCH PRODUCT
A solvent-directed stereoselective and electrocatalytic synthesis of diisoeugenol.
Tsuyoshi SaitohTakashi YamamotoKeisuke NabaAnton WiebeYasuaki EinagaKenshin NakaharaSiegfried R. WaldvogelBarbara RiehlBarbara Riehlsubject
010402 general chemistry01 natural sciencesCatalysisCoupling reactionlaw.inventionMetalchemistry.chemical_compoundlawMaterials ChemistryMoleculeElectrolysis010405 organic chemistryMetals and AlloysGeneral ChemistryCombinatorial chemistry0104 chemical sciencesSurfaces Coatings and FilmsElectronic Optical and Magnetic MaterialsSolventIsoeugenolchemistryvisual_artElectrodeCeramics and Compositesvisual_art.visual_art_mediumStereoselectivitydescription
A stereoselective and electrocatalytic coupling reaction of isoeugenol has been reported for the first time in a 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP)/boron-doped diamond (BDD) electrode system. This particular C-C bond formation and diastereoselectivity is driven by a solvate interaction between the radical species and another isoeugenol molecule. Due to an electrocatalytic cycle, only understoichiometric amounts of charge are necessary. Since electric current is directly employed as the oxidant, the reaction is metal and reagent-free. In addition, the electrolysis can be conducted in a very simple undivided beaker-type cell under constant current conditions. Therefore, the protocol is easy to use, suitable for scale-up, and inherently safe.
year | journal | country | edition | language |
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2018-02-28 | Chemical communications (Cambridge, England) |