Journal
TETRAHEDRON LETTERS
Volume 56, Issue 42, Pages 5727-5730Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2015.08.083
Keywords
Silver oxide; Nanoparticle; Azide; Alkyne; 1,3-Dipolar cycloadditions
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1,3-Dipolar cycloadditions between a number of azides and monosubstituted acetylenes have been carried out in the presence of catalytic amounts of silver(l) oxide nanoparticles. 4-Substituted 1,2,3-triazoles were usually the only products, while the presence of electron-withdrawing groups onto the azide moiety caused a loss of regioselectivity giving mixtures of 4- and 5-substituted 1,2,3-triazoles. A novel catalytic cycle has been proposed to rationalize this latter 'non-click' behaviour. (C) 2015 Elsevier Ltd. All rights reserved.
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