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Synthesis 2011(17): 2737-2742  
DOI: 10.1055/s-0030-1260061
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York

‘Click’ Synthesis of Nonsymmetrical 4,4′-Bis(1,2,3-triazolium) Salts

Jesus M. Aizpurua*a, Maialen Sagartzazu-Aizpuruaa, Itxaso Azcunea, José I. Mirandaa, Zaira Monasterioa, Eva García-Lecinab, Raluca M. Fratilac
a Departamento de Química Orgánica-I, Universidad del País Vasco UPV/EHU, Joxe Mari Korta R&D Center, Avda Tolosa-72, 20018 San Sebastián, Spain
Fax: +34(943)015959; e-Mail: jesusmaria.aizpurua@ehu.es;
b Departamento de Tratamientos de Superficie, CIDETEC-ik4, Paseo Miramón-196, 20009 San Sebastián, Spain
c Faculty of Science and Technology, SupraMolecular Chemistry & Technology (SMCT), University of Twente, 7500 AE Enschede, The Netherlands
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Publication History

Received 5 March 2011
Publication Date:
09 June 2011 (online)

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Abstract

Nonsymmetrically substituted 4,4′-bis(1,2,3-triazolium) salts were prepared in a totally site-specific manner by copper(I)-catalyzed ‘click’ [2+3] cycloaddition of 3-alkyl-4-ethynyl-1,2,3-triazolium salts with alkyl and aryl azides. Competition experiments demonstrated that triazolium alkynes were more reactive than their triazole counterparts in CuAAC reactions, especially with aromatic azides. The N-alkylation site integrity was maintained in all the triazolium salts prepared.

Key words

alkylation - catalysis - cycloaddition - heterocycles - 1,2,3-triazolium salts

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