Amination-reduction reaction as simple protocol for potential boronic molecular receptors. Insight in supramolecular structure directed by weak interactions

作者：Adamczyk Wozniak Agnieszka^*; Madura Izabela; Pawelko Alicja; Sporzynski Andrzej; Zubrowska Anna; Zyla Jacek

来源：CENTRAL EUROPEAN JOURNAL OF CHEMISTRY, 2011, 9(2): 199-205.

DOI：10.2478/s11532-010-0142-8

• Boronic acids
• Benzoxaboroles
• X-ray structure
• Hirshfeld surface
• Supramolecular structure

The synthesis of the potential molecular receptors in the amination-reduction reaction has been investigated within the model system comprising (2-formylphenyl) boronic acid and morpholine. The 3-amine substituted benzoxaborole was identified to be the intermediate of the synthesis and the unsubstituted benzoxaborole as the by-product resulting from reduction of the starting material. The insight into the reactivity of the starting materials as well as the intermediate benzoxaborole enabled significant rise in the yield of 2-(aminomethyl) phenylboronic acids synthesis. The solid state structure of 2-(piperidylmethyl) phenylboronic acid has been re-determined, and the description of the molecule and the crystal is given. The supramolecular layer structure directed by the weak C-H center dot center dot center dot O and C-H center dot center dot center dot pi interactions was identified and scrutinized based on the geometry and Hirshfeld surface analyses

• 出版日期2011-4