Nucleophilic displacement reactions of 5'-derivatised nucleosides in a vibration ball mill.
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.
School of Chemistry and Chemical Engineering, Queen's University Belfast, David Keir Building, Stranmillis Road, Belfast BT9 5AG, UK.
Olga
O
Eguaogie
School of Chemistry and Chemical Engineering, Queen's University Belfast, David Keir Building, Stranmillis Road, Belfast BT9 5AG, UK.
Patrick F
PF
Conlon
School of Chemistry and Chemical Engineering, Queen's University Belfast, David Keir Building, Stranmillis Road, Belfast BT9 5AG, UK.
Francesco
F
Ravalico
School of Chemistry and Chemical Engineering, Queen's University Belfast, David Keir Building, Stranmillis Road, Belfast BT9 5AG, UK.
Jamie S T
JS
Sweet
School of Chemistry and Chemical Engineering, Queen's University Belfast, David Keir Building, Stranmillis Road, Belfast BT9 5AG, UK.
Thomas B
TB
Elder
Durham University, Department of Chemistry, Lower Mountjoy, Stockton Road, Durham DH1 3LE, UK.
Louis P
LP
Conway
School of Chemistry and Chemical Engineering, Queen's University Belfast, David Keir Building, Stranmillis Road, Belfast BT9 5AG, UK.
Marc E
ME
Lennon
Durham University, Department of Chemistry, Lower Mountjoy, Stockton Road, Durham DH1 3LE, UK.
David R W
DR
Hodgson
School of Chemistry and Chemical Engineering, Queen's University Belfast, David Keir Building, Stranmillis Road, Belfast BT9 5AG, UK.
Joseph S
JS
Vyle
ball mill; chalcogen; mechanochemistry; nucleophilic substitution; nucleoside