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

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

doi:10.3762/bjoc.13.11

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

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

Authors

Olga Eguaogie

Patrick F. Conlon

Francesco Ravalico

Jamie S.T. Sweet

Thomas B. Elder

Louis P. Conway

Marc E. Lennon

Professor David Hodgson d.r.w.hodgson@durham.ac.uk
Professor

Joseph S. Vyle

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.

Citation

Eguaogie, O., Conlon, P. F., Ravalico, F., Sweet, J. S., Elder, T. B., Conway, L. P., …Vyle, J. S. (2017). Nucleophilic displacement reactions of 5′-derivatised nucleosides in a vibration ball mill. Beilstein Journal of Organic Chemistry, 13, 87-92. https://doi.org/10.3762/bjoc.13.11

Journal Article Type	Article
Acceptance Date	Dec 30, 2016
Online Publication Date	Jan 13, 2017
Publication Date	Jan 13, 2017
Deposit Date	Jan 3, 2017
Publicly Available Date	Jan 16, 2017
Journal	Beilstein Journal of Organic Chemistry
Print ISSN	1860-5397
Publisher	Beilstein-Institut
Peer Reviewed	Peer Reviewed
Volume	13
Pages	87-92
DOI	https://doi.org/10.3762/bjoc.13.11

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© 2017 Eguaogie et al.; licensee Beilstein-Institut.
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