Silver(I) oxide nanoparticles as a catalyst in the azide–alkyne cycloaddition. Issue 42 (14th October 2015)

• Record Type: Journal Article
• Authors: Ferretti, Anna M.; Ponti, Alessandro; Molteni, Giorgio
• Is Part Of: Tetrahedron letters. Volume 56:Issue 42(2015)
• Page Start: 5727
• Page End: 5730
• Publication Date: 2015-10-14
• Subjects: Silver oxide -- Nanoparticle -- Azide -- Alkyne -- 1, 3-Dipolar cycloadditions; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.08.083
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: 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.