Issue 20, 2011
From the journal:

Chemical Communications

Overcoming hydrolytic sensitivity and low solubility of phosphitylation reagents by combining ionic liquids with mechanochemistry†

Christopher Hardacre,*a   Haifeng Huang,a   Stuart L. James,a   Marie E. Migaud,*b   Sarah E. Normana  and  William R. Pitnerc  

* Corresponding authors

a School of Chemistry and Chemical Engineering, Queen's University, Belfast, UK
E-mail: c.hardacre@qub.ac.uk
Fax: +44 (0)28 90974687

b School of Pharmacy, Queen's University, Belfast, UK
E-mail: m.migaud@qub.ac.uk
Fax: +44 (0)28 90247794

c Merck KGaA, PC R & D Ionic Liquids, Frankfurter Str. 250, Darmstadt, Germany

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.

Graphical abstract: Overcoming hydrolytic sensitivity and low solubility of phosphitylation reagents by combining ionic liquids with mechanochemistry

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Article information

DOI
https://doi.org/10.1039/C1CC11025J
Article type
Communication
Submitted
22 Feb 2011
Accepted
04 Apr 2011
First published
18 Apr 2011

Chem. Commun., 2011,47, 5846-5848

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Overcoming hydrolytic sensitivity and low solubility of phosphitylation reagents by combining ionic liquids with mechanochemistry

C. Hardacre, H. Huang, S. L. James, M. E. Migaud, S. E. Norman and W. R. Pitner, Chem. Commun., 2011, 47, 5846 DOI: 10.1039/C1CC11025J

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