Arylboronic acids with the amino group in ortho position are widely used as carbohydrate receptors [1, 2]. They can be synthesized from o-formylphenylboronic acid by reduction of corresponding Schiff base:

An alternative method is the reaction of benzoxaborole I with amines:

Benzoxaborole I is a stable compound, easy to obtain from o-tolueneboronic acid by bromination and hydrolysis.

The spectroscopic characterization of the products II will be presented.

[1] T. D. James, S. Shinkai, Top. Curr. Chem. 2002, 218, 159.

[2] J. F. Callan, A. P. de Silva, D. C. Magri, Tetrahedron 2005, 61, 8551.

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1. Intermolecular Donor-Acceptor Interactions of B(OH)₂ Group in Phenylboronic Acids – Important or Not?
2. Structure of ortho-Substituted Arylboronic Acids - a Key to Sugar Receptor Activity