Multidimensional SuFEx Click Chemistry: Sequential Sulfur(VI) Fluoride Exchange Connections of Diverse Modules Launched From An SOF4 Hub
| Autor: | K. Barry Sharpless, Peng Wu, Suhua Li, John E. Moses |
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| Rok vydání: | 2017 |
| Předmět: |
Thionyl tetrafluoride
010405 organic chemistry Chemistry Difluoride chemistry.chemical_element General Chemistry 010402 general chemistry 01 natural sciences Sulfur Catalysis 0104 chemical sciences chemistry.chemical_compound Covalent bond Polymer chemistry Click chemistry Organic chemistry Fluoride |
| Zdroj: | Angewandte Chemie International Edition. 56:2903-2908 |
| ISSN: | 1433-7851 |
| DOI: | 10.1002/anie.201611048 |
| Popis: | Sulfur(VI) fluoride exchange (SuFEx) is a new family of click chemistry based transformations that enable the synthesis of covalently linked modules via SVI hubs. Here we report thionyl tetrafluoride (SOF4 ) as the first multidimensional SuFEx connector. SOF4 sits between the commercially mass-produced gases SF6 and SO2 F2 , and like them, is readily synthesized on scale. Under SuFEx catalysis conditions, SOF4 reliably seeks out primary amino groups [R-NH2 ] and becomes permanently anchored via a tetrahedral iminosulfur(VI) link: R-N=(O=)S(F)2 . The pendant, prochiral difluoride groups R-N=(O=)SF2 , 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. |
| Databáze: | OpenAIRE |
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