Nucleophilic displacement reactions of 5′-derivatised nucleosides in a vibration ball mill

Olga Eguaogie, Patrick F. Conlon, Francesco Ravalico, Jamie Sweet, Thomas B. Elder, Louis P. Conway, Marc E. Lennon, David R.W. Hodgson, Joseph S. Vyle

Research output: Contribution to journalArticle

5 Citations (Scopus)
279 Downloads (Pure)

Abstract

Vibration ball-milling in a zirconia-lined vessel afforded clean and quantitative nucleophilic displacement reactions between 4-methoxybenzylthiolate salts and nucleoside 5′-halides or 5′-tosylates in five to 60 minutes. Under these conditions, commonly-encountered nucleoside cyclisation byproducts (especially of purine nucleosides) were not observed. Liquid-assisted grinding of the same 5'-iodide and 5′-tosylate substrates with potassium selenocyanate in the presence of DMF produced the corresponding 5′-selenocyanates in variable yields over the course of between one and eleven hours thereby avoiding the preparation and use of hygroscopic tetrabutylammonium salts.
Original languageEnglish
Pages (from-to)87–92
Number of pages6
JournalBeilstein Journal of Organic Chemistry
Volume13
DOIs
Publication statusPublished - 13 Jan 2017

Keywords

  • ball mill
  • chalcogen
  • mechanochemistry
  • ; nucleophilic substitution
  • nucleoside

ASJC Scopus subject areas

  • Organic Chemistry

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