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

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Abstract

© 2017 Eguaogie et al.; licensee Beilstein-Institut. 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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Eguaogie, O., Conlon, P. F., Ravalico, F., Sweet, J. S. T., 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

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