Trifluoromethyl propargylamines react with various azide derivatives to afford 1,4-disubstituted 1,2,3-triazoles through a Huisgen 1,3-dipolar cycloaddition. The reaction is catalyzed by a Cu(I) species in acetonitrile, and the corresponding products are obtained in good yields. This process thus offers an entry to new trifluoromethyl peptidomimetics as interesting scaffolds.

The explosively-growing applications of the Cu-catalyzed Huisgen 1,3-dipolar cycloaddition reaction between organic azides and alkynes (CuAAC) have stimulated an impressive number of reports, in the last years, focusing on recoverable variants of the homogeneous or quasi-homogeneous catalysts. Recent advances in the field are reviewed, with particular emphasis on systems immobilized onto polyme...

Preparation of several acyclonucleosides containing both a difluoromethylphosphonate group and a triazole moiety is described starting from a difluorophosphonosulfide. The key step of the synthesis involves a copper(I)-catalyzed Huisgen 1-3 dipolar cycloaddition between difluorophosphonylated azides and propargylated nucleobases derived from thymine and 2-amino-6-chloropurine.

A family of artificial nucleosides has been developed by applying the Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition. Starting from 2-deoxy-β-D-glycosyl azide as a common precursor, three bidentate nucleosides have been synthesized. The 1,2,3-triazole involved in all three nucleobases is complemented by 1,2,4-triazole (TriTri), pyrazole (TriPyr), or pyridine (TriPy). Molecular structures of ...

The synthesis and properties of multifunctional thioureas bearing a variety of functional groups at a position remote from the thiourea moiety are described. A 1,5-disubstituted triazole tether connected with a thiourea and another functional group was synthesized via ruthenium catalyzed Huisgen cycloaddition. We demonstrate the utility of the synthetic thioureas as asymmetric catalysts and pro...

Aromatic ynamines or N-alkynylheteroarenes are highly reactive alkyne components in Cu-catalyzed Huisgen [3 + 2] cycloaddition ("click") reactions. This enhanced reactivity enables the chemoselective formation of 1,4-triazoles using the representative aromatic ynamine N-ethynylbenzimidazole in the presence of a competing aliphatic alkyne substrate. The unique chemoselectivity profile of N-ethyn...

The chiral-discriminating abilities of new triazole-linked host compounds (6, 7) toward amino acid esters were evaluated by the FABMS/EL-guest method. Two types of host appending saccharide derivatives were synthesized by the copper-catalyzed Huisgen-1,3-dipolar cycloaddition (CuAAC). Host compounds binding constants and chiral-discriminating abilities toward the enantiomeric alanine esters wer...

A copper-(I)-catalyzed variation of the Huisgen 1,3-dipolar cycloaddition has been applied to lead the in living-cell mass-spectrometry based identification of protein targets of oleocanthal, a natural metabolite daily ingested by millions of people. Chemical proteomics revealed heat-shock proteins, HSP70 and HSP90, as main oleocanthal interactors in living systems. These two proteins are invol...

[Structure: see text] A novel procedure for catalyst recycling is described. Copper(I)-based catalysts, equipped with an affinity tag, are isolated from crude reaction mixtures on the basis of quadruple hydrogen-bonding interactions using a resin functionalized with complementary affinity tags. Recycled catalysts were successfully used to catalyze a tandem Sonogashira coupling/5-endo-dig cycliz...

Copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition between terminal alkynes and azides – also known as the copper (Cu)-catalyzed Azide-Alkyne Cycloaddition (CuAAC) – has been used in the syntheses of molecular compounds with diverse structures and functions, owing to its functional group tolerance, facile execution, and mild reaction conditions under which it can be promoted. Recently, rotax...