Halo-1,2,3-triazolium salts as halogen bond donors for the activation of imines in dihydropyridinone synthesis

Mikk Kaasik, Andrus Metsala, Sandra Kaabel, Kadri Kriis, Ivar Järving, Tonis Kanger*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

40 Citations (Scopus)

Abstract

In the past decade halogen bond (XB) catalysis has gained considerable attention. Halo-triazoles are known XB donors, yet few examples detail their use as catalysts. As a continuation of our previous work the catalytic properties of substituted enantiomerically pure halo-triazolium salts were explored in the reaction between an imine and Danishefsky's diene leading to the formation of dihydropyridinone. The catalytic activity of the XB donors was highly dependent on the choice of the halogen atom and on the counterion. Also, it was found that impurities in the diene affected the rate of the reaction.

Original languageEnglish
Pages (from-to)4295-4303
Number of pages9
JournalJournal of Organic Chemistry
Volume84
Issue number7
DOIs
Publication statusPublished - 5 Apr 2019
MoE publication typeA1 Journal article-refereed

Fingerprint

Dive into the research topics of 'Halo-1,2,3-triazolium salts as halogen bond donors for the activation of imines in dihydropyridinone synthesis'. Together they form a unique fingerprint.

Cite this