Benzylaminoboronic Acids - Synthesis and Characterization

Anna Żubrowska ,  Andrzej Sporzyński 

Warsaw University of Technology, Faculty of Chemistry, Noakowskiego 3, Warszawa 00-664, Poland

Abstract

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:

ania1.jpg

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

ania2.jpg

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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Presentation: poster at 18th Conference on Physical Organic Chemistry, Posters, by Anna Żubrowska
See On-line Journal of 18th Conference on Physical Organic Chemistry

Submitted: 2006-06-20 15:01
Revised:   2009-06-07 00:44
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