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Synthesis 2009(1): 127-132  
DOI: 10.1055/s-0028-1083271
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Coordination-Induced Intramolecular Double Cyclization: Synthesis of Boron-Bridged Dipyridylvinylenes and Dithiazolylvinylenes

Qiang Zhao, Hongyu Zhang, Atsushi Wakamiya, Shigehiro Yamaguchi*
Department of Chemistry, Graduate School of Science, Nagoya University, Furo, Chikusa, Nagoya 464-8602, Japan
Fax: +81(52)7895947; e-Mail: yamaguchi@chem.nagoya-u.ac.jp;
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Publication History

Received 22 October 2008
Publication Date:
12 December 2008 (online)

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Abstract

Di(heteroaryl)acetylenes having a pyridyl or thiazolyl as the heteroaryl group underwent a reaction with bromodibenzoborole to produce coordination complexes, which were further treated with water to promote the intramolecular cascade double cyclization to produce the dibenzoborolyl-bridged ladder di(heteroaryl)vinylenes. For the thiazolyl derivative, further derivatization at the terminal positions produced a bis(dimesitylboryl)-substituted derivative. The ladder molecules prepared showed an intense emission in the fluorescence spectra as well as reversible reduction waves at low reduction potentials in the cyclic voltammetry.

Key words

boron - acetylene - N-heteroaryl - cascade cyclization - π-electron systems

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