Cationic 1,2,3 triazolium alkynes : components to enhance 1,4 regioselective azide rlkyne cycloaddition reactions
Cationic 1,2,3 triazolium alkynes : components to enhance 1,4 regioselective azide rlkyne cycloaddition reactions
Date
2016
Authors
Yuri Reyes, 0000-0003-3945-2111
Journal Title
Journal ISSN
Volume Title
Publisher
Universidad Autónoma Metropolitana. Unidad Lerma
Abstract
Description
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).
Keywords
BIOLOGÍA Y QUÍMICA