Li, S., Wu, P., Moses, J. E., Sharpless, K. B. (March 2017) Multidimensional SuFEx Click Chemistry: Sequential Sulfur(VI) Fluoride Exchange Connections of Diverse Modules Launched From An SOF(4) Hub. Angew Chem Int Ed Engl, 56 (11). pp. 2903-2908. ISSN 1433-7851 (Print)1433-7851
Abstract
Sulfur(VI) fluoride exchange (SuFEx) is a new family of click chemistry based transformations that enable the synthesis of covalently linked modules via S(VI) hubs. Here we report thionyl tetrafluoride (SOF(4) ) as the first multidimensional SuFEx connector. SOF(4) sits between the commercially mass-produced gases SF(6) and SO(2) F(2) , and like them, is readily synthesized on scale. Under SuFEx catalysis conditions, SOF(4) reliably seeks out primary amino groups [R-NH(2) ] and becomes permanently anchored via a tetrahedral iminosulfur(VI) link: R-N=(O=)S(F)(2) . The pendant, prochiral difluoride groups R-N=(O=)SF(2) , in turn, offer two further SuFExable handles, which can be sequentially exchanged to create 3-dimensional covalent departure vectors from the tetrahedral sulfur(VI) hub.
| Item Type: | Paper |
|---|---|
| Additional Information: | Angewandte Chemie (International ed. in English) |
| CSHL Authors: | |
| Communities: | CSHL labs > Moses lab |
| Depositing User: | Matthew Dunn |
| Date: | 6 March 2017 |
| Date Deposited: | 08 Jan 2021 17:24 |
| Last Modified: | 08 Jan 2021 17:24 |
| PMCID: | PMC5434761 |
| URI: | https://repository.cshl.edu/id/eprint/39572 |
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