1,3-Dipolar cycloadditions between a number of azides and monosubstituted acetylenes have been carried out in the presence of catalytic amounts of silver(I) 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.
Silver(I) oxide nanoparticles as a catalyst in the azide–alkyne cycloaddition / A.M. Ferretti, A. Ponti, G. Molteni. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 56:42(2015 Oct), pp. 5727-5730.
Silver(I) oxide nanoparticles as a catalyst in the azide–alkyne cycloaddition
G. Molteni
2015
Abstract
1,3-Dipolar cycloadditions between a number of azides and monosubstituted acetylenes have been carried out in the presence of catalytic amounts of silver(I) 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.File | Dimensione | Formato | |
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