Visible-Light-Induced Click Chemistry

A rapid and catalyst‐free cycloaddition system for visible‐light‐induced click chemistry is reported. A readily accessible photoreactive 2H‐azirine moiety was designed to absorb light at wavelengths above 400 nm. Irradiation with low‐energy light sources thus enables efficient small‐molecule synthes...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2015-08, Vol.54 (35), p.10284-10288
Main Authors: Mueller, Jan O., Schmidt, Friedrich G., Blinco, James P., Barner-Kowollik, Christopher
Format: Article
Language:English
Subjects:
Accessibility
azirine
Catalysis
Catalysts
Chromophores
Click Chemistry
Cycloaddition
Irradiation
Light
Light sources
Low energy
Photochemistry
polymer ligation
Polymers - chemistry
Synthesis
visible light
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Summary:A rapid and catalyst‐free cycloaddition system for visible‐light‐induced click chemistry is reported. A readily accessible photoreactive 2H‐azirine moiety was designed to absorb light at wavelengths above 400 nm. Irradiation with low‐energy light sources thus enables efficient small‐molecule synthesis with a diverse range of multiple‐bond‐containing compounds. Moreover, in order to demonstrate the efficiency of the current approach, quantitative ligation of the photoactivatable chromophore with functional polymeric substrates was performed and full conversion with irradiation times of only 1 min at ambient conditions was achieved. The current report thus presents a highly efficient method for applications involving selective cycloaddition to electron‐deficient multiple‐bond‐containing materials. Quick as a flash: A rapid and catalyst‐free cycloaddition system for visible‐light‐induced click chemistry at ambient conditions is reported. Irradiation of a 2H‐azirine moiety with low‐energy light sources enables efficient small‐molecule synthesis with a diverse range of multiple‐bond‐containing compounds, as well as rapid quantitative ligation of the photoactivatable chromophore with polymeric substrates.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201504716