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

Christopher Hardacre; Haifeng Huang; Stuart L. James; Marie E. Migaud; Sarah E. Norman; William R. Pitner

doi:10.1039/c1cc11025j

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

Christopher Hardacre^*, Haifeng Huang, Stuart L. James, Marie E. Migaud, Sarah E. Norman, William R. Pitner

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	5846-5848
Number of pages	3
Journal	Chemical Communications
Volume	47
Issue number	20
DOIs	https://doi.org/10.1039/c1cc11025j
Publication status	Published - 28 May 2011

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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.",

author = "Christopher Hardacre and Haifeng Huang and James, {Stuart L.} and Migaud, {Marie E.} and Norman, {Sarah E.} and Pitner, {William R.}",

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AU - Hardacre, Christopher

AU - Huang, Haifeng

AU - James, Stuart L.

AU - Migaud, Marie E.

AU - Norman, Sarah E.

AU - Pitner, William R.

PY - 2011/5/28

Y1 - 2011/5/28

N2 - 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.

AB - 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.

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DO - 10.1039/c1cc11025j

M3 - Article

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

Abstract

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