The synthesis of 2-(arylaminomethyl)phenylboronic acid via an amination–reduction reaction has been investigated within a model system comprising 2-formylphenylboronic acid and N-ethylaniline. Adoption of the appropriate reaction conditions influences the reactivity of 2-formylphenylboronic acid, enabling efficient synthesis of so-far unobtainable 2-(arylaminomethyl)phenylboronic compounds. The first crystal structure of the aromatic amine derivative has been determined and described.
Adamczyk-Wozniak, A., Fratila, R. M., Madura, I. D., Pawelko, A., Sporzynski, A., Tumanowicz, M., ... Zyla, J. (2011). Reactivity of 2-formylphenylboronic acid toward secondary aromatic amines in amination–reduction reactions. Tetrahedron letters, 52(49), 6639-6642. https://doi.org/10.1016/j.tetlet.2011.10.008