title: Site-Selective N-Dealkylation of 1,2,3-Triazolium Salts: A Metal-Free Route to 1,5-Substituted 1,2,3-Triazoles and Related Bistriazoles.
abstract: N3-Alkylation of 1-(pivaloyloxymethyl)-1,2,3-triazoles with alkyl triflates carrying latent "click" functionality, followed by a nucleophile-promoted N1-dealkylation of the resulting strongly electrophilic intermediate triazolium salts, provides an efficient route to 1,5-disubstituted 1,2,3-triazoles. The azide and alkyne groups incorporated by N-alkylation can be submitted to further copper-catalyzed azide-alkyne and Huisgen cycloadditions to provide bis(1,2,3-triazoles) with unprecedented 1,5/1,4 substitution patterns.
authors.affiliation: Departamento de Química Orgánica-I, Universidad del País Vasco UPV/EHU Joxe Mari Korta R&D Center , Avda Tolosa-72, 20018 San Sebastián, Spain.
authors.forename: Zaira
authors.initials: Z
authors.lastname: Monasterio
authors.affiliation: Departamento de Química Orgánica-I, Universidad del País Vasco UPV/EHU Joxe Mari Korta R&D Center , Avda Tolosa-72, 20018 San Sebastián, Spain.
authors.forename: Aitziber
authors.initials: A
authors.lastname: Irastorza
authors.affiliation: Departamento de Química Orgánica-I, Universidad del País Vasco UPV/EHU Joxe Mari Korta R&D Center , Avda Tolosa-72, 20018 San Sebastián, Spain.
authors.forename: José I
authors.initials: JI
authors.lastname: Miranda
authors.affiliation: Departamento de Química Orgánica-I, Universidad del País Vasco UPV/EHU Joxe Mari Korta R&D Center , Avda Tolosa-72, 20018 San Sebastián, Spain.
authors.forename: Jesus M
authors.initials: JM
authors.lastname: Aizpurua