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

Jesus M. Aizpurua; Maialen Sagartzazu-Aizpurua; Itxaso Azcune; José I. Miranda; Zaira Monasterio; Eva García-Lecina; Raluca M. Fratila

doi:10.1055/s-0030-1260061

SPECIALTOPIC

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

Jesus M. Aizpurua*^a, Maialen Sagartzazu-Aizpurua^a, Itxaso Azcune^a, José I. Miranda^a, Zaira Monasterio^a, Eva García-Lecina^b, Raluca M. Fratila^c
^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

Abstract

Alle Artikel dieser Rubrik

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

Volltext

Referenzen

References

<A NAME="RC25211SS-1A">1a</A> Tornoe CW. Christensen C. Meldal M. J. Org. Chem. 2002, 67: 3057

<A NAME="RC25211SS-1B">1b</A> Rostovtsev VV. Green LG. Fokin VV. Sharpless KB. Angew. Chem. Int. Ed. 2002, 41: 2596

<A NAME="RC25211SS-1C">1c</A> Meldal M. Tornoe CW. Chem. Rev. 2008, 108: 2952

<A NAME="RC25211SS-2A">2a</A> Hanelt S. Liebscher J. Synlett 2008, 1058

<A NAME="RC25211SS-2B">2b</A> Khan SS. Hanelt S. Liebscher J. ARKIVOC 2009, (xii): 193

<A NAME="RC25211SS-2C">2c</A> Jeong Y. Ryu J.-S. J. Org. Chem. 2010, 75: 4183

<A NAME="RC25211SS-2D">2d</A> Fletcher JT. Keeney ME. Walz SE. Synthesis 2010, 3339

<A NAME="RC25211SS-2E">2e</A> Nakamura T. Ogata K. Fukuzawa S.-I. Chem. Lett. 2010, 39: 920

<A NAME="RC25211SS-2F">2f</A> Yacob Z. Shah J. Leistner J. Liebscher J. Synlett 2008, 2342

<A NAME="RC25211SS-2G">2g</A> Shah J. Khan SS. Blumenthal H. Liebscher J. Synthesis 2009, 3975

<A NAME="RC25211SS-3">3</A> Khan SS. Shah J. Liebscher J. Tetrahedron 2010, 66: 5082

<A NAME="RC25211SS-4A">4a</A> Coutrot F. Busseron E. Chem. Eur. J. 2008, 14: 4784

<A NAME="RC25211SS-4B">4b</A> Jiang Y. Guo J.-B. Chen C.-F. Org. Lett. 2010, 12: 4248

<A NAME="RC25211SS-4C">4c</A> Kilah NL. Wise MD. Serpell CJ. Thompson AL. White NG. Christensen KE. Beer PD. J. Am. Chem. Soc. 2010, 132: 11893

<A NAME="RC25211SS-5A">5a</A> Mathew P. Neels A. Albrecht M. J. Am. Chem. Soc. 2008, 130: 13534

<A NAME="RC25211SS-5B">5b</A> Guisado-Barrios G. Bouffard J. Donnadieu B. Bertrand G. Angew. Chem. Int. Ed. 2010, 49: 4759

<A NAME="RC25211SS-5C">5c</A> Lalrempuia R. McDaniel ND. Müller-Bunz H. Bernhard S. Albrecht M. Angew. Chem. Int. Ed. 2010, 49: 9765

<A NAME="RC25211SS-5D">5d</A> Kilpin KJ. Paul USD. Lee A.-L. Crowley JD. Chem. Commun. 2011, 47: 328

<A NAME="RC25211SS-5E">5e</A> Prades A. Peris E. Albrecht M. Organometallics 2011, 30: 1162

<A NAME="RC25211SS-5F">5f</A> Poulain A. Canseco-Gonzalez D. Hynes-Roche R. Müller-Bunz H. Schuster O. Stoeckli-Evans H. Neels A. Albrecht M. Organometallics 2011, 30: 1021

<A NAME="RC25211SS-6">6</A> Khan SS. Liebscher J. Synthesis 2010, 2609

<A NAME="RC25211SS-7">7</A> Schulze B. Friebe C. Hager MD. Günther W. Köhn U. Jahn BO. Görls H. Schubert US. Org. Lett. 2010, 12: 2710

<A NAME="RC25211SS-8">8</A> Palomo C. Aizpurua JM. Balentova E. Azcune I. Santos JI. Jimenez-Barbero J. Cañada J. Miranda JI. Org. Lett. 2008, 10: 2227

<A NAME="RC25211SS-9">9</A> For the first synthesis of nonsymmetrically substituted 4,4′-bis(1,2,3-triazoles), see: Fiandanese V. Bottalico D. Marchese G. Punzi A. Capuzzola F. Tetrahedron 2009, 65: 10573

<A NAME="RC25211SS-10">10</A> Aizpurua JM. Azcune I. Fratila RM. Balentova E. Sagartzazu-Aizpurua M. Miranda JI. Org. Lett. 2010, 12: 1584

<A NAME="RC25211SS-11">11</A> Wamhoff H. 1,2,3-Triazoles and their Benzo Derivatives, In Comprehensive Heterocyclic Chemistry Vol. 5: Katritzky AR. Rees CW. Pott KT. Pergamon Press; Oxford: 1984. p.669

<A NAME="RC25211SS-12">12</A> Schubert US. Hoogenboom R. Hager MD. Winter A. Friebe C. Happ B. Chem. Asian J. 2009, 4: 154

<A NAME="RC25211SS-13">13</A> Elamari H. Meganem F. Herscovici J. Girard C. Tetrahedron Lett. 2011, 52: 658