Abstract
| Original language | English |
|---|---|
| Pages (from-to) | 87–92 |
| Number of pages | 6 |
| Journal | Beilstein Journal of Organic Chemistry |
| Volume | 13 |
| DOIs | |
| Publication status | Published - 13 Jan 2017 |
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Keywords
- ball mill
- chalcogen
- mechanochemistry
- ; nucleophilic substitution
- nucleoside
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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 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 -