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J Org Chem. 2006 Dec 22;71(26):9791-6.

Heterogeneous diazo-transfer reaction: a facile unmasking of azide groups on amine-functionalized insoluble supports for solid-phase synthesis.

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  • 1School of Chemistry and Biochemistry, Parker H. Petit Institute for Bioengineering and Biosciences, Georgia Institute of Technology, Atlanta, Georgia 30332-0400, USA. aoyelere@gatech.edu


Solid-supported azides are commonly generated through direct nucleophilic displacement of appropriately activated supports by the azide ion. This reaction usually proceeds rather sluggishly under harsh conditions. Here, we report that triflyl azide rapidly reacts with a series of amine-functionalized solid supports to generate azide-coated supports under mild conditions. Further, we demonstrate that the "azide coat" allows facile loading of alkyne-functionalized leader nucleoside monomers by click chemistry. Finally, we show that the nucleoside-functionalized supports are suitable for solid-phase oligonucleotide synthetic applications. The approach herein described extends the scope of the amine-azide conversion reaction and may be adaptable for the introduction of azide to diverse amine-terminated solid supports that are not easily accessible by the conventional nucleophilic displacement method.

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