Science of Synthesis

Harris, T.; Alabugin, I. V., Science of Synthesis: Click Chemistry, (2021) 1, 337.

General Introduction

Metal-catalyzed click chemistry[‌1‌–‌3‌] offers a modular way to connect functional building blocks to form hybrid molecular structures in high yields and high selectivity. While the prototypical click reaction, the copper-catalyzed azide–alkyne cycloaddition (CuAAC),[‌4‌–‌8‌] has made a tremendous impact in interdisciplinary scientific research, its utility is hampered by the deleterious effects of copper salts in living systems[‌9‌–‌12‌] and toward redox-sensitive nanoparticles[‌13‌–‌15‌] where toxic and redox-active species should be avoided. The strain-promoted azide–alkyne cycloaddition (SPAAC)[‌16‌,‌17‌] overcame these limitations for bioconjugation[‌18‌–‌21‌] and surface functionalization[‌22‌–‌24‌] by using cycloalkynes in a catalyst-free manner. Many incarnations of cycloalkynes have been developed[‌25‌–‌28‌] to tailor their chemical and spectroscopic[‌29‌–‌31‌] properties for the specific applications.[‌32‌]

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References