The synthesis of organic compounds by electric current serves as an environmentally friendly and sustainable approach as it avoids the generation of reagent waste and may facilitate unusual reaction-pathways as well.^[1] The direct electrochemical C,H amination of activated aromatic compounds was first reported and elaborated by the Yoshida group in 2013.^[2]The introduction of an amino moiety is performed via anodic pyridination of the corresponding methoxy substituted aromatic compounds followed by ring-opening of the obtained pyridinium intermediates. We successfully applied this state-of-the-art amination method to less activated aromatic substrates e.g. alkylated arenes. However, using carbon felt anodes only moderate yields were obtained. Therefore, boron-doped diamond as anode material that shows a higher performance at more positive potentials was used.^[3] In initial findings, this novel and innovative electrode material has demonstrated an outstanding performance in electrochemical amination reactions of simple alkylated arenes. Materials like platinum and glassy carbon show no performance at all. We present the scope and CV studies of this interesting electrosynthetic method.

References:

[1]    a) B. A. Frontana-Uribe, R. D. Little, J. G. Ibanez, A. Palma, R. Vasquez-Medrano, Green Chem. 2010, 12, 2099-2119; b) J. I. Yoshida, K. Kataoka, R. Horcajada, A. Nagaki, Chem. Rev. 2008, 108, 2265-2292.

[2]   T. Morofuji, A. Shimizu, J. I. Yoshida, J. Am. Chem. Soc. 2013, 135, 5000-5003; S. R. Waldvogel, S. Möhle, Angew. Chem. Int. Ed. 2015, 54, 6398-6399.

[3]   B. Elsler, D. Schollmeyer, K. M. Dyballa, R. Franke, S. R. Waldvogel, Angew. Chem. Int. Ed.2014, 53, 5210-5213.