0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via
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]

Meee eeeeeee eeeeeeeee eeeeeeee eeeeeeeee eeeeeeeeee ee eeeeee eee eeeeeeeeeeee, eeeeeeee eee eeeeeeeee eee eeeeeeeeeee MMMMM eeeeeeeeee eeeeeee eeeeee eeeeeeeeeee eee eeeee eeeeeeee eeeeeeeeeeeee, eee eeeeeeeeee eeeeeeee ee eeeeeee eeeeeeeeeeeeee eeee eeeeeeeeeeee. Meee eeeeeeeee eee eeeeeeeee eeee eee eeee eeee ee eee eeeeee ee eeeeee eeeeeeeeeeee eee eeeee eeeeeeee ee eeeeee eeeeeeeeeee eeeeeeee eeeeeeeee eee eee eee eeeeeeeeeee ee eee eeeeeeeeeeee.