title: Cationic 1,2,3-Triazolium Alkynes: Components To Enhance 1,4-Regioselective Azide-Alkyne Cycloaddition Reactions.
abstract: 4-Alkynyl-1,2,3-triazolium cations undergo thermal [3 + 2] cycloaddition reactions with azides roughly 50- to 100-fold faster than comparable noncharged alkynes. Further, the reaction is highly 1,4-regioselective (dr up to 99:1) owing to the selective stabilization of 1,4-TS transition states via conjugative π-acceptor assistance of the alkyne triazolium ring. The novel cationic triazolium alkynes also accelerate the CuAAC reaction to provide bis(1,2,3-triazoles) in an "ultrafast" way (<5 min).
authors: 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: Zaira
authors: Z
authors: Monasterio
authors: 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: Maialen
authors: M
authors: Sagartzazu-Aizpurua
authors: 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: José I
authors: JI
authors: Miranda
authors: Universidad Autónoma Metropolitana UAM , Hidalgo Poniente-46 Col. La Estación, 52006 Lerma de Villada, Mexico.
authors: Yuri
authors: Y
authors: Reyes
authors: 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: Jesus M
authors: JM
authors: Aizpurua