A modular synthetic method for bis- and tris-1,2,3-triazoles that include a benzotriazole structure was developed on the basis of sequential azide-aryne and azide-alkyne cycloadditions. The key to success was efficient halogen-metal exchange reaction-mediated generation of aryne from ortho-iodoaryl triflates bearing a base-sensitive terminal alkyne moiety, which was achieved using trimethylsily...

Two highly efficient protocols for the regioselective synthesis of 2-substituted 4-alkenyl- and 4-aryl-1,2,3-triazoles by the palladium-catalyzed C-H functionalization of 1,2,3-triazole N-oxides are reported. A possible pathway of direct alkenylation with 1-octene and vinyl acetate is discussed.

New 1,2,4-triazoles (2) having a difluoro(substituted sulfonyl)methyl moiety were designed and synthesized via alpha,alpha-difluoro-alpha-(substituted thio)acetophenones (3). Compounds (2) showed potent antifungal activities against C. albicans, C. krusei, A. flavus and A. fumigatus in vitro and against C. albicans in vivo for oral and i.v. administrations. Especially, (-)-2a, (-)-2b and (-)-2d...

1,2-Dipole Tf2C=CH2 is generated in situ and immediately reacts at room temperature with an azide to afford previously unknown 4-trifluoromethanesulfonyl 1,2,3-triazoles through a stepwise [3+2] cycloaddition reaction. Noteworthily, this mild and powerful uncatalyzed protocol is highly regio- and chemoselective.

A four-folded azidation of tetrakis(4-iodophenyl)methane and -adamantane leads to stable organic azides, but yet energetic materials, measured by differential scanning calorimetry (DSC). The rigid and symmetrical structures can be useful for new polymer and nanomaterial developments in material sciences as well as bioconjugations, after 1,3-dipolar cycloaddition reactions with terminal alkynes ...

The remarkable activity displayed by copper(I)phosphinite complexes of general formula [CuBr(L)] in two challenging cycloadditions is reported: a) the one pot azidonation/cycloaddition from boronic acids, NaN3 and terminal alkynes; b) the cycloaddition of azides and iodoalkynes. These airstable catalysts led to very good results in both cases and the expected triazoles could be isolated pure un...

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.