Click Reactions
Click chemistry, or click reaction, was introduced by Sharpless and co-workers at The Scripps Research Institute in 2001, and further expounded upon by Moses and Becer[1]. In October 2022, the Nobel Prize in chemistry was awarded to "click chemistry" and its major chemists. The name “click” implies that linking molecular pieces is as easy as “clicking” together the two pieces of a buckle. The buckle works no matter what is attached to it, as long as its two pieces can reach each other, and the components of the buckle can make a connection only with each other[2]. With the introduction of bioorthogonal reactions, click reactions were required to be bioorthogonal and not affect other biological environments. Click reactions have a profound impact on many fields of modern chemistry such as bioconjugation, materials science, and drug discovery[3].
Characteristics of Click Reactions
Click reactions share the following characteristics:
- Click reactions require only simple reaction conditions, such as solventless conditions or water.
- Many reagents for click reactions are derived from alkenes and alkynes, which are easily available.
- Click reactions are strongly exothermic due to the high-energy reactants or strongly stable products.
- Click reactions are usually fusion processes (without byproducts) or condensation processes (producing water as a byproduct).
- Most click reactions involve the formation of carbon-heteroatom (mostly N, O, and S) bonds, in contrast to modern synthetic organic chemistry, which emphasizes the formation of carbon-carbon bonds.
Common Click Reactions
In most reports, click reactions were limited to copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reactions. This is a narrow understanding and interpretation of click reactions, and the broader click reactions are as follows. If you want to know more about the relevant information, please click on the following links.
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References
- Sinha, A.K.; Equbal, D. Thiol-ene reaction as a sharping stone of click chemistry: recent advances in synthetic aspects and mechanistic studies of antiMarkovnikov-selective hydrothiolation of olefins. Asian Journal of Organic Chemistry. 2019, 1(8): 32-47.
- Finn, M. G.; Fokin, V.V. Click chemistry: function follows form. Chemical Society Reviews. 2010, 4(39): 1231-1232.
- Moses, J.E.; Moorhouse, A.D. The growing applications of click chemistry. Chemical Society Reviews. 2007, 24(36): 1249-1262.
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