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

MetadataDetails
Publication Date2016-02-12
JournalEuropean Journal of Organic Chemistry
AuthorsSebastian Herold, Sabine Möhle, Michael Zirbes, Frank Richter, Hartmut Nefzger
InstitutionsCovestro (Germany), Johannes Gutenberg University Mainz
Citations71

Abstract 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 sp 3 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.