Copper Nanoparticles Cycloaddition of Terminal Acetylenes with Carbohydrate Azide Khaoula Hajlaoui 1 • Naoufel Ben Hamadi 1,2 • Moncef Msaddek 1 Received: 5 February 2015 / Accepted: 15 March 2015 Ó Springer Science+Business Media New York 2015 Abstract Copper nanoparticles have been found to ef- fectively catalyse the asymmetric synthesis of 1,2,3-tria- zoles from cycloaddition of carbohydrate azide and terminal acetylenes in water. In all case the cycloaddition is accomplished with complete regioselectivity. Graphical Abstract Keywords Carbohydrates  Copper nanoparticles  Cycloaddition  Heterogeneous catalysis  Triazoles  Water 1 Introduction As appreciation for the biological importance of carbo- hydrates has increased, so have efforts to develop methods for the synthesis of biologically relevant oligosaccharides, glycoconjugates, and analogues thereof [1–5]. Among the more challenging synthetic targets are aminoglycosides and their derivatives. Heterocycles containing 1,2,3-triazole ring systems are known to posses biological activity including anti-HIV [6], anti- allergic [7], antifungal [8], antiviral [9], antimicrobial activity [10]. 1,2,3-Triazole moieties are useful building blocks in chemistry and can be modified to exhibit im- portant roles in pharmacological applications due to their stability to light, moisture, oxygen, and metabolism in the body [11]. Moreover these moieties have found a wide range of applications in industry as dyes, corrosion inhibitors, photostabilizers, photographic materials, and agrochemicals [12]. Therefore, attention has been given to the development of new and more efficient synthetic pathways to a diverse array of 1,2,3-triazole pharma- cophores. The search for new biologically active com- pounds containing 1,2,3-triazole ring is still continuing and is relevant. One example is the 1,3-dipolar cy- cloaddition reaction between an azide and a terminal alkyne in the presence of a copper-based catalyst to give the corresponding triazole [13]. This method, developed by Meldal [14] and Sharpless [15], is potentially useful in the design and synthesis of new compounds with N N N O R O O O O O N 3 O O O O O + CuNPs (1%) H 2 O, rt R O & Naoufel Ben Hamadi bh_naoufel@yahoo.fr 1 Laboratory of Synthesis Heterocyclic and Natural Substances, Department of Chemistry, Faculty of Sciences of Monastir, Boulevard of Environment, 5000 Monastir, Tunisia 2 Chemistry Department, College of Science, IMSIU (Al-Imam Mohammad Ibn Saud Islamic University), Riyadh 11623, Kingdom of Saudi Arabia 123 Catal Lett DOI 10.1007/s10562-015-1521-8