title: Overcoming hydrolytic sensitivity and low solubility of phosphitylation reagents by combining ionic liquids with mechanochemistry.
abstract: Ionic liquids have been used in combination with ball milling on a range of chlorophosphoramidite reagents to phosphitylate nucleosides and 2-deoxynucleosides. The enhanced stability offered by the ionic liquid mediated processes combined with efficient mass transfer induced by ball milling has enabled excellent yields to be obtained even when using small dialkyl amino groups as well as the more commonly used diisopropylamino protection.
authors.affiliation: School of Chemistry and Chemical Engineering, Queen's University, Belfast, UK. c.hardacre@qub.ac.uk
authors.forename: Christopher
authors.initials: C
authors.lastname: Hardacre
authors.forename: Haifeng
authors.initials: H
authors.lastname: Huang
authors.forename: Stuart L
authors.initials: SL
authors.lastname: James
authors.forename: Marie E
authors.initials: ME
authors.lastname: Migaud
authors.forename: Sarah E
authors.initials: SE
authors.lastname: Norman
authors.forename: William R
authors.initials: WR
authors.lastname: Pitner
mesh_terms: D003839:Deoxyadenosines / Q000737:chemistry; D006868:Hydrolysis; D052578:Ionic Liquids / Q000737:chemistry*; D009705:Nucleosides / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry*; D012995:Solubility
chemical_list: D003839:Deoxyadenosines; D052578:Ionic Liquids; D009705:Nucleosides; D009943:Organophosphorus Compounds; C434331:phosphoramidite; C058118:2'-deoxyadenosine