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4.1 Strain-Promoted Azide–Alkyne Cycloaddition (SPAAC): Background, Substrate Preparation, and Reactivity

DOI: 10.1055/sos-SD-235-00143

Harris, T.; Alabugin, I. V.Science of Synthesis: Click Chemistry, (20211337.

General Introduction

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

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