Smedley, Christopher J, Giel, Marie‐Claire, Fallon, Thomas, Moses, John E (July 2023) Ethene‐1,1‐disulfonyl Difluoride (EDSF) for SuFEx Click Chemistry: Synthesis of SuFExable 1,1‐Bissulfonylfluoride Substituted Cyclobutene Hubs. Angewandte Chemie International Edition, 135 (30). ISSN 0044-8249
Abstract
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 Cs2CO3‐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.
| Item Type: | Paper |
|---|---|
| Subjects: | chemistry > techniques > click chemistry > Accelerated SuFEx Click Chemistry chemistry chemistry > techniques > click chemistry chemistry > techniques |
| CSHL Authors: | |
| Communities: | CSHL Cancer Center Program CSHL labs > Moses lab CSHL Cancer Center Program > Cellular Communication in Cancer Program |
| SWORD Depositor: | CSHL Elements |
| Depositing User: | CSHL Elements |
| Date: | 24 July 2023 |
| Date Deposited: | 22 Sep 2023 15:05 |
| Last Modified: | 29 Apr 2024 20:10 |
| PMCID: | PMC10958772 |
| Related URLs: | |
| URI: | https://repository.cshl.edu/id/eprint/40975 |
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