Azide terminally functional poly(methyl methacrylate)s (Mn = 4000-6000, PDI = 1.21-1.28) have been prepared by living radical polymerization and successfully reacted with alkynes in a Huisgen cycloaddition (click) reaction in one pot using the same catalyst for both processes.

Triazoles are an important class of heterocyclic compounds. In recent years 1,2,3-triazoles gained more and more interest due to their diverse biological activities and synthetic methodology [1 – 3]. An efficient approach for constructing the 1,2,3-triazole unit is the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction, which was discovered independently by the groups of Sharpless ...

A chemical library of 1,2,3-triazole fused carbohydrate mimetics was constructed. To synthesize enantiomerically pure mimetics, we developed a stereo- or diastereodivergent synthetic route from D-glucose, D-mannose and D-galactose as chiral sources. In this synthesis, an In(OTf)(3)-catalyzed tandem azidation-1,3-dipolar cycloaddition reaction of 1,1-dimethoxyhex-5-yne derivatives with TMSN(3) w...

A modular approach to the construction of monocationic quaternary N-heteroaromatic frameworks was developed capitalizing on a direct pyridine-type nitrogen quaternization followed by metal-catalyzed [2+2+2] cycloaddition with gaseous acetylene. The flexibility of the route is demonstrated on 12 diverse scaffolds based on pyridinium, quinolinium, thiazolium, benzothiazolium, imidazolium, and pyr...

Abstract Metal-catalyzed [2+2+2] cycloaddition is a powerful tool that allows rapid construction of functionalized 6-membered carbo- and heterocycles in single step through an atom-economical process with high functional group tolerance. The reaction usually regio- chemoselective although selectivity issues can still be challenging for intermolecular reactions involving the cross-[2+2+2] two or...

In this article, we report the functionalization of alkyne-terminated alkyl monolayers on Si(100) using "click" chemistry, specifically, the Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction of azides with surface-bound alkynes. Covalently immobilized, structurally well-defined acetylene-terminated organic monolayers were prepared from a commercially available terminal diyne species us...

The inside cover picture, designed by Fabrice Goursaud, holder of a PhD in organic chemistry and recently graduated from art school, illustrates the stereoselective synthesis tetrahydro[2,3-b]pyridine frameworks via one-pot metal-organo relay catalysis. strategy, which involves gold-catalyzed cycloisomerization chiral amine mediated cycloaddition reaction, provides targeted molecules yields ran...

The CoII-catalyzed [2+2+2] cycloaddition of functionalized diynes and phosphaalkynes resulting in the formation an array structurally interesting phosphinines is reported. A combination 1,2-bis(diphenylphosphino)benzene (dppbenz) CoI2 turned out to be most suitable active catalyst system under microwave reaction conditions. Chemoselective cyclizations presence nitriles have been observed, a num...

Abstract A new synthesis strategy for the preparation of cellulose derivative-based chiral selectors and subsequent mild immobilization onto pre-functionalized silica gel are introduced, utilizing Cu(I)-catalyzed alkyne-azide Huisgen cycloaddition (“ click ”) chemistry. 3,5-dimethylphenyl carbamate derivative carrying propynyl groups was prepared by a combination carbonate aminolysis isocyanate...