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 ...

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...

Nicotine-based ionic liquid has been used as a green catalyst for pyridine-catalyzed Huisgen reaction. It promoted addition of dimethylacetylenedicarboxylate to aldehydes or N-tosyl imines leading to efficient synthesis of 2-benzoylfumarates and 1-azadienes respectively under pyridine free odorless ionic liquid conditions. The improved results were obtained in terms of enhanced yields, with min...

Nicotine-based ionic liquid has been used as a green catalyst for pyridine-catalyzed Huisgen reaction. It promoted addition of dimethylacetylenedicarboxylate to aldehydes or N-tosyl imines leading to efficient synthesis of 2-benzoylfumarates and 1-azadienes respectively under pyridine free odorless ionic liquid conditions. The improved results were obtained in terms of enhanced yields, with min...

SN2 rection between 4-(tert-butyldimethylsilyl)hex-5-yn-1-yl 4-methylbenzenesulfonate and NaN3 in DMF at 80 °C provided (6-azidohex-1-yn-3-yl)(tert-butyl)dimethylsilane intermediate, which underwent situ intramolecular thermal Huisgen azide–alkyne cycloaddition reaction. This one-pot process gave 4-(tert-butyldimethylsilyl)-4,5,6,7-tetrahydro-[1,2,3]triazolo[1,5-a]pyridine 78% yield.

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...

In recent years there has been renewed activity in the literature concerning the 1,3-dipolar cycloaddition reaction (1,3-DCR) of organic azides (R-N₃) with alkynes (R'-C≡CH) to form 1,2,3-triazoles, i.e. the Huisgen synthesis. The use of catalytic Cu(I) leads to a dramatic rate enhancement (up to 10(7)-fold) and exclusive synthesis of the 1,4-disubstituted 1,2,3-triazole product. The reaction, ...