Journal
TETRAHEDRON LETTERS
Volume 49, Issue 17, Pages 2824-2827Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.02.115
Keywords
5-substituted 1H-tetrazole; [3+2] cycloaddition; nitrite; copper catalyst; copper azide; trimethylsilyl azide
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The [3+2] cycloaddition between various nitrites and trimethylsityl azide proceeds smoothly in the presence of a Cu(I) catalyst in DMF/MeOH, to give the corresponding 5-substituted 1H-tetrazoles in good to high yields. The reaction most probably proceeds through the in situ formation of a copper azide species, followed by a successive [3+2] cycloaddition with the nitrites. (C) 2008 Elsevier Ltd. All rights reserved.
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