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

doi:10.3762/bjoc.13.11

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

School of Chemistry and Chemical Engineering

Research output: Contribution to journal › Article

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 language	English
Pages (from-to)	87–92
Number of pages	6
Journal	Beilstein Journal of Organic Chemistry
Volume	13
DOIs	https://doi.org/10.3762/bjoc.13.11
Publication status	Published - 13 Jan 2017

Keywords

ball mill
chalcogen
mechanochemistry
; nucleophilic substitution
nucleoside

ASJC Scopus subject areas

Organic Chemistry

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10.3762/bjoc.13.11Licence: CC BY

Nucleophilic displacement reactions of 5′-derivatised nucleosides in a vibration ball mill
© 2017 Eguaogie et al.; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (http://www.beilstein-journals.org/bjoc)
Final published version, 272 KBLicence: CC BY

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@article{81800f5aee284c8ea011d06f6cb2b4c0,

title = "Nucleophilic displacement reactions of 5′-derivatised nucleosides in a vibration ball mill",

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.",

keywords = "ball mill, chalcogen, mechanochemistry, ; nucleophilic substitution, nucleoside",

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

year = "2017",

month = jan,

day = "13",

doi = "10.3762/bjoc.13.11",

language = "English",

volume = "13",

pages = "87–92",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

}

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 journal › Article

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.

PY - 2017/1/13

Y1 - 2017/1/13

N2 - 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.

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.

KW - ball mill

KW - chalcogen

KW - mechanochemistry

KW - ; nucleophilic substitution

KW - nucleoside

U2 - 10.3762/bjoc.13.11

DO - 10.3762/bjoc.13.11

M3 - Article

VL - 13

SP - 87

EP - 92

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

SN - 1860-5397

ER -