- Title
- Ethene-1,1-disulfonyl Difluoride (EDSF) for SuFEx Click Chemistry: Synthesis of SuFExable 1,1-Bissulfonylfluoride Substituted Cyclobutene Hubs
- Creator
- Smedley, Christopher J.; Giel, Marie-Claire; Fallon, Thomas; Moses, John E.
- Relation
- Angewandet Chemie International Edition Vol. 62, Issue 30, no. e202303916
- Publisher Link
- http://dx.doi.org/10.1002/anie.202303916
- Publisher
- Wiley-VCH Verlag GmbH & Co. KGaA
- Resource Type
- journal article
- Date
- 2023
- Description
- We present the synthesis of 1,1-bis(fluorosulfonyl)-2-(pyridin-1-ium-1-yl)ethan-1-ide, a bench-stable precursor to ethene-1,1-disulfonyl difluoride (EDSF). The novel SuFEx reagent, EDSF, is demonstrated in the preparation of 26 unique 1,1-bissulfonylfluoride substituted cyclobutenes via a cycloaddition reaction. The regioselective click cycloaddition reaction is rapid, straightforward, and highly efficient, enabling the generation of highly functionalized 4-membered ring (4MR) carbocycles. These carbocycles are valuable structural motifs found in numerous bioactive natural products and pharmaceutically relevant small molecules. Additionally, we showcase diversification of the novel cyclobutene cores through selective Cs2 CO3 -activated SuFEx click chemistry between a single S-F group and an aryl alcohol, yielding the corresponding sulfonate ester products with high efficiency. Finally, density functional theory calculations offer mechanistic insights about the reaction pathway.
- Subject
- click chemistry; cycloaddition; cyclobutenes; suFEx; sulfur-fluoride exchange
- Identifier
- http://hdl.handle.net/${Handle}
- Identifier
- uon:51256
- Identifier
- ISSN:1433-7851
- Language
- eng
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