Chemoselective preparation of disymmetric bistriazoles from bisalkynes |
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Authors: | Hichem Elamari Faouzi MeganemJean Herscovici Christian Girard |
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Affiliation: | a Unité de Pharmacologie Chimique, Génétique et Imagerie, UMR8151 CNRS—U1022 INSERM, Chimie ParisTech (Ecole Nationale Supérieure de Chimie de Paris), 11, rue Pierre et Marie Curie, 75005 Paris, France b Laboratoire de Chimie Organique & Applications, Faculté des Sciences de Bizerte, 7021 Jarzouna, Bizerte, Tunisia |
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Abstract: | Best of both worlds, molecules bearing two alkyne groups, activated and unactivated, can selectively react on the activated one in a copper-free version of Huisgen’s reaction to form a first triazole ring, with a good selectivity toward the 1,4-isomer, which is solely isolated by a simple trituration procedure. The other alkyne function is then submitted to the selective reaction using a polymer-supported copper(I) catalyst to form a second triazole ring. This gave access to disymmetric bistriazoles without the need of protection using simple, easy, and fast procedures. |
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Keywords: | Huisgen&rsquo s reaction Click chemistry Activation Alkyne Azide |
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