6533b824fe1ef96bd128094a

RESEARCH PRODUCT

Electrochemical Amination of Less-Activated Alkylated Arenes Using Boron-Doped Diamond Anodes

Hartmut NefzgerFrank RichterMichael ZirbesSabine MöhleSebastian HeroldSiegfried R. Waldvogel

subject

Green chemistry010405 organic chemistryChemistryOrganic ChemistryCationic polymerizationDiamondchemistry.chemical_elementengineering.materialAlkylation010402 general chemistryElectrochemistry01 natural sciencesCombinatorial chemistry0104 chemical scienceschemistry.chemical_compoundAnilineengineeringOrganic chemistryPhysical and Theoretical ChemistryCarbonAmination

description

The anodic C–H amination of aromatic compounds is a powerful and versatile method for the synthesis of aniline derivatives. By using boron-doped diamond (BDD) anodes, a method initially described by Yoshida et al. for electron-rich arenes was expanded to less-activated aromatic systems e.g., simple alkylated benzene derivatives. Anodes based on sp3 carbon seem to be the key for the electrochemical amination reaction. The corresponding primary anilines are obtained in good yields. Despite the cationic intermediates of the electrolytic reaction tert-butyl moieties are tolerated.

https://doi.org/10.1002/ejoc.201600048