1,3-dipolar cycloaddition of azides with electron-deficient alkynes under mild condition in water

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We report a simple synthetic protocol for the 1,3-dipolar cycloaddition of azides with electron-deficient alkynes. Alkyne with at least one neighboring electron-withdrawing group proceeds with the cycloaddition successfully without any catalysts at room temperature in water. Under this simple condition, we evaluated a series of small molecule model reactions and then coupled an azido-DNA molecule with electron-deficient alkynes for the formation of [1,2,3]-triazole heterocycle, providing a potential method for introducing functional groups to DNA under biological conditions. (C) 2004 Elsevier Ltd. All rights reserved.
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Issue Date
2004-04
Language
English
Article Type
Article
Keywords

TERMINAL ALKYNES; CLICK CHEMISTRY; CUCURBITURIL; CATALYSIS

Citation

TETRAHEDRON LETTERS, v.45, no.15, pp.3143 - 3146

ISSN
0040-4039
DOI
10.1016/j.tetlet.2004.02.089
URI
http://hdl.handle.net/10203/8846
Appears in Collection
CBE-Journal Papers(저널논문)
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