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Chemoselective preparation of disymmetric bistriazoles from bisalkynes
Authors:Hichem Elamari  Faouzi MeganemJean Herscovici  Christian Girard
Institution: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
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.
Keywords:Huisgen&rsquo  s reaction  Click chemistry  Activation  Alkyne  Azide
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