CuAAC Click Reaction

The Huisgen 1,3-dipolar cycloaddition reaction of organic azides and alkynes has gained considerable attention in recent years due to the introduction of Cu(I) catalysis by Tornøe and Meldal in 2001, leading to a major improvement in both rate and regioselectivity of the reaction, as realized independently by Meldal and Sharpless laboratories^[1]. This reaction is a typical example of click reactions, known as the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) click reaction that allows the synthesis of compounds containing a triazole ring. The schematic diagram of the CuAAC click reaction is shown in scheme 1.

Scheme 1. Schematic diagram of the CuAAC click reaction.

Advantages

CuAAC click reaction is widely used in the field of material science, biomedicine and other fields, providing new ideas for the synthesis of a variety of compounds, and even has potential value in the treatment of some diseases. The main advantages or characteristics of CuAAC click reaction are as follows.

• High reaction rate:

The reaction rate of the CuAAC click reaction is 107 to 108 times higher than that of the non-catalytic Huisgen 1,3-dipolar cycloaddition reaction.

• High condition tolerance:

CuAAC click reaction is insensitive to water and reacts over a wide range of temperatures and pH (4-12).

• Cheap raw materials:

Reagents of CuAAC click reaction include azides, terminal alkynes, and copper catalysts, which are readily available and inexpensive.

• High selectivity:

CuAAC click reaction efficiently couples two molecular entities functionalized by azide and ethynyl, respectively, to regiospecifically form a 1,2,3-triazole linkage^[2].

• Others:

Other advantages of the CuAAC click reaction include high yield, high tolerance to multiple functional groups, and the ease of separation and purification of the final product.

What Can We Do?

As a leading customer-focused company, Alfa Chemistry has experienced experts and professional R & D laboratories. For many years, we have been focusing on reagent development and potential application exploration of the CuAAC click reaction. If you have questions about the CuAAC click reaction, please contact us. We will draw upon our wide range of advantages and high-quality products to create customized, scalable, efficient solutions for your research.

References

1. Meldal, M.; Tornøe, C.W. Cu-catalyzed azide-alkyne cycloaddition. Chemical Reviews. 2008, 8(108): 2952-3015.
2. Zhu, L.; et al. On the mechanism of copper(I)-catalyzed azide-alkyne cycloaddition. Chemical Reviews. 2016, 16: 1501-1517.