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Fluoride-Mediated Nucleophilic Aromatic Amination of Chloro-1<i>H</i>-1,2,3-triazolium Salts

Daiya Kase, Ryosuke Haraguchi

2021Organic Letters22 citationsDOI

Abstract

-1,2,3-triazolium salts with aliphatic amines. The reaction proceeded under mild reaction conditions to provide amino-1,2,3-triazolium salts with various functional groups, which can be utilized for further transformations. Moreover, it was found that an amino-1,2,3-triazolium salt was transformed via deprotonation into the N-heterocyclic imine (NHI), which exhibited the excellent catalytic activity for the cyanosilylation of acetophenone with trimethylsilyl cyanide.

Topics & Concepts

ChemistryAminationNucleophileAcetophenoneDeprotonationSalt (chemistry)FluorideImineOrganic chemistryTrimethylsilyl cyanideCatalysisNucleophilic additionMedicinal chemistryInorganic chemistryIonClick Chemistry and ApplicationsN-Heterocyclic Carbenes in Organic and Inorganic ChemistryChemical Synthesis and Analysis
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