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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

Zaira Monasterio, Aitziber Irastorza, José I. Miranda and Jesus M. Aizpurua*

*Departamento de Química Orgánica-I, Universidad del País Vasco UPV/EHU Joxe Mari Korta R&D Center, Avda Tolosa-72, 20018 San Sebastián, Spain, Email: jesusmaria.aizpuruaehu.es

Z. Monasterio, A. Irastorza, J. I. Miranda, J. M. Aizpurua, Org. Lett., 2016, 18, 2515-2518.

DOI: 10.1021/acs.orglett.6b01177 (free Supporting Information)


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Abstract

N3-Alkylation of 1-(pivaloyloxymethyl)-1,2,3-triazoles with alkyl triflates, followed by a nucleophile-promoted N1-dealkylation of the resulting strongly electrophilic intermediate triazolium salts, provides 1,5-disubstituted 1,2,3-triazoles.

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Key Words

1,2,3-triazoles


ID: J54-Y2016