Developments in the Reactivity of 2-Methylimidazolium Salts

Daniela Peixoto, Margarida Figueiredo, Manoj B. Gawande, Marta C Corvo, Gerd Vanhoenacker, Carlos A M Afonso, Luisa M Ferreira, Paula S. Branco

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

Unexpected and unusual reactivity of 2-methylimidazolium salts toward aryl-N-sulfonylimines and aryl aldehydes is here reported. Upon reaction with aryl-N-sulfonylimines, the addition product, arylethyl-2-imidazolium-1-tosylamide (3), is formed with moderate to good yields, while upon reaction with aldehydes, the initial addition product (6) observed in NMR and HPLC-MS experimental analysis is postulated by us as an intermediate to the final conversion to carboxylic acids. Studies in the presence and absence of molecular oxygen allow us to conclude that the imidazolium salts is crucial for the oxidation. A detailed mechanistic study was carried out to provide insights regarding this unexpected reactivity.

Original languageEnglish
Pages (from-to)6232-6241
Number of pages10
JournalJournal of Organic Chemistry
Volume82
Issue number12
DOIs
Publication statusPublished - 16 Jun 2017

Keywords

  • N-HETEROCYCLIC CARBENES
  • C BOND-CLEAVAGE
  • VITRO ANTITUMOR-ACTIVITY
  • IONIC LIQUIDS
  • ENZOIN CONDENSATION
  • EFFICIENT
  • CATALYSIS
  • ALDEHYDES
  • DESIGN
  • TRANSFORMATIONS

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