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

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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Zhang, H.; Karasawa, T.; Yamada, H.; Wakamiya, A.; Yamaguchi, S., unpublished results.

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Crystallographic data for 4a and 4b have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 706194 and 706195, respectively. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: [phone] or e-mail: [e-mail]].