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

4 Citations (Scopus)
222 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

Fingerprint

Ball mills
Nucleosides
Salts
Purine Nucleosides
Cyclization
Ball milling
Iodides
Byproducts
Liquids
Substrates
selenocyanic acid
zirconium oxide
tetrabutylammonium

Keywords

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

Cite this

Eguaogie, Olga ; Conlon, Patrick F. ; Ravalico, Francesco ; Sweet, Jamie ; Elder, Thomas B. ; Conway, Louis P. ; Lennon, Marc E. ; Hodgson, David R.W. ; Vyle, Joseph S. / Nucleophilic displacement reactions of 5′-derivatised nucleosides in a vibration ball mill. In: Beilstein Journal of Organic Chemistry. 2017 ; Vol. 13. pp. 87–92.
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Nucleophilic displacement reactions of 5′-derivatised nucleosides in a vibration ball mill. / Eguaogie, Olga; Conlon, Patrick F.; Ravalico, Francesco; Sweet, Jamie; Elder, Thomas B.; Conway, Louis P.; Lennon, Marc E.; Hodgson, David R.W.; Vyle, Joseph S.

In: Beilstein Journal of Organic Chemistry, Vol. 13, 13.01.2017, p. 87–92.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Nucleophilic displacement reactions of 5′-derivatised nucleosides in a vibration ball mill

AU - Eguaogie, Olga

AU - Conlon, Patrick F.

AU - Ravalico, Francesco

AU - Sweet, Jamie

AU - Elder, Thomas B.

AU - Conway, Louis P.

AU - Lennon, Marc E.

AU - Hodgson, David R.W.

AU - Vyle, Joseph S.

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Y1 - 2017/1/13

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AB - 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.

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KW - chalcogen

KW - mechanochemistry

KW - ; nucleophilic substitution

KW - nucleoside

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DO - 10.3762/bjoc.13.11

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JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

SN - 1860-5397

ER -