Synthesis and structural analysis of conjugated benzoxazaborine derivatives

[Display omitted] •A novel boron-containing compound, benzoxazaborine, was synthesized.•The obtained benzoxazaborines were reasonably stable to hydrolysis.•The oxazaborine ring was the highly planar structure.•The BN bond length indicated an extended π-conjugated system. Benzoxazaborine derivatives...

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Bibliographic Details
Published in:Tetrahedron letters 2018-11, Vol.59 (47), p.4153-4157
Main Authors: Ohishi, Tomoyuki, Igarashi, Kaori, Kadosono, Hiroki, Kikkawa, Shoko, Azumaya, Isao, Yokoyama, Akihiro
Format: Article
Language:English
Subjects:
2-Aminobenzyl alcohol
Benzoxazaborine
Boronic acid
Condensation reaction
Reversible reaction
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Summary:[Display omitted] •A novel boron-containing compound, benzoxazaborine, was synthesized.•The obtained benzoxazaborines were reasonably stable to hydrolysis.•The oxazaborine ring was the highly planar structure.•The BN bond length indicated an extended π-conjugated system. Benzoxazaborine derivatives were synthesized by the dehydration condensation reaction of 2-aminobenzyl alcohols with arylboronic acids. The insensitivity of the benzoxazaborines to hydrolysis allowed these compounds to be isolated by silica gel column chromatography. The single crystal X-ray structural analysis demonstrated the highly planar structure of the benzoxazaborine unit, and the BN bond length indicated an extended π-conjugated system.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2018.10.022