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Review | Special issue | Vol 99, No. 2, 2019, pp.725-741
Published online, 29th January, 2019
DOI: 10.3987/REV-18-SR(F)4
Mini-Review: Organic Catalysts in the 1,3-Dipolar Cycloaddition Reactions of Nitrile Oxides

Silvia Roscales* and Joaquín Plumet*

*Complutense University, Faculty of Chemistry, Organic Chemistry Department, Ciudad Universitaria, 28040, Madrid, Spain


In 1961, Huisgen categorized the nitrile oxides (NOs) as a member of a broader class of 1,3-dipoles that were capable of undergoing 1,3-dipolar cycloaddition (DC) reactions. Nevertheless, the cycloaddition (CA) reactions of NOs to alkenes and alkynes are in many cases hampered by the tendency to the dimerization of the NO to the related furoxan (1,2,5-oxadiazole 2-oxide). In addition, although monosubstituted alkenes and alkynes show high regioselectivity in their cycloadditions with NOs, 1,2-disubstituted derivatives often give mixtures of regioisomers. Catalyzed NOs cycloadditions constitute in many cases an appropriate response to these problems and, in particular, the metal catalyzed cycloaddition reactions have been extensively used. However, the cost, toxicity and removal of trace amounts of the metal residues from desired products is quite costly and challenging, while crucial, especially in the pharmaceutical industry. Obviously, alternative pathways under metal-free conditions to fulfill the metal-catalyzed reactions are highly appealing. The present review is devoted to the consideration of the use of organic molecules as catalysts for 1,3-dipolar cycloaddition reactions of nitrile oxides.