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A New Portal to SuFEx Click Chemistry: A Stable Fluorosulfuryl Imidazolium Salt Emerging as an “F−SO2+” Donor of Unprecedented Reactivity, Selectivity, and Scope
Abstract
Sulfuryl fluoride, SO 2 F 2, has been found to derivatize phenols in all kinds of environments, even those in highly functional molecules. We now report that a solid fluorosulfuryl imidazolium triflate salt delivers the same “F−SO 2+” fragment to Nu−H acceptor groups in the substrates. However, this triflate salt is a far more reactive fluorosulfurylating agent than SO 2 F 2 and displays selectivity preferences of its own. Moreover, the new azolium triflate reagent reacts once with primary amines and anilines before the reaction stops. On the other hand, with triethylamine and two equivalents of the “F−SO 2+” donor present, it proceeds on to the bis(fluorosulfuryl)imides in good yield—two important conversions that we have never seen with sulfuryl fluoride as the electrophile.
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Cites
Broad-Spectrum Kinase Profiling in Live Cells with Lysine-Targeted Sulfonyl Fluoride Probes
Zhao, Q., Ouyang, X., Wan, X., Gajiwala, K. S., Kath, J. C., Jones, L. H., Burlingame, A. L., & Taunton, J. (2017) · Journal of the American Chemical Society · doi:10.1021/jacs.6b08536 · Cited by 388
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Cu(I)-Catalyzed Click Chemistry in Glycoscience and Their Diverse Applications
Agrahari, A. K., Bose, P., Jaiswal, M. K., Rajkhowa, S., Singh, A. S., Hotha, S., Mishra, N., & Tiwari, V. K. (2021) · Chemical Reviews · doi:10.1021/acs.chemrev.0c00920 · Cited by 445
Modular click chemistry libraries for functional screens using a diazotizing reagent
Meng, G., Guo, T., Ma, T., Zhang, J., Shen, Y., Sharpless, K. B., & Dong, J. (2019) · Nature · doi:10.1038/s41586-019-1589-1 · Cited by 357
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Metadata
- Authors
- Guo, T., Meng, G., Zhan, X., Yang, Q., Ma, T., Xu, L., Sharpless, K. B., & Dong, J.
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2018-01-25
- Volume
- 57
- Issue
- 10
- Pages
- 2605-2610
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W2778299120
- Cited by
- 234
- References
- 1
- FWCI
- 5.20
- Type
- journal article
- Language
- en
- Open access
- closed
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- Guo, T., Meng, G., Zhan, X., Yang, Q., Ma, T., Xu, L., Sharpless, K. B., & Dong, J. (2018). A New Portal to SuFEx Click Chemistry: A Stable Fluorosulfuryl Imidazolium Salt Emerging as an “F−SO2+” Donor of Unprecedented Reactivity, Selectivity, and Scope. Angewandte Chemie International Edition. https://doi.org/10.1002/anie.201712429
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