Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 143, Issue 36, Pages 14495-14501Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.1c06014
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- ETH Zuich
- Swiss Chemical Industry (SSCI)
- FWF [J4461]
- Deutsche Forschungsgemeinschaft (DFG)
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The study presents a modular approach to novel arylazotriazole photoswitches, with the synthesis of a wide range of organic compounds through copper-catalyzed cycloaddition reactions. These compounds serve as stable intermediates for the synthesis of complex molecules derived from natural products or drugs.
We report a modular approach toward novel arylazotriazole photoswitches and their photophysical characterization. Addition of lithiated TIPS-acetylene to aryldiazonium tetrafluoroborate salts gives a wide range of azoacetylenes, constituting an underexplored class of stable intermediates. In situ desilylation transiently leads to terminal arylazoacetylenes that undergo copper-catalyzed cycloadditions (CuAAC) with a diverse collection of organoazides. These include complex molecules derived from natural products or drugs, such as colchicine, taxol, tamiflu, and arachidonic acid. The arylazotriazoles display near-quantitative photoisomerization and long thermal Z-half-lives. Using the method, we introduce for the first time the design and synthesis of a diacetylene platform. It permits implementation of consecutive and diversity-oriented approaches linking two different conjugants to independently addressable acetylenes within a common photoswitchable azotriazole. This is showcased in the synthesis of several photoswitchable conjugates, with potential applications as photoPROTACs and biotin conjugates.
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