SuFEx Chemistry of Thionyl Tetrafluoride (SOF4 ) with Organolithium Nucleophiles: Synthesis of Sulfonimidoyl Fluorides, Sulfoximines, Sulfonimidamides, and Sulfonimidates
| Autor: | K. Barry Sharpless, Peng Wu, Bing Gao, Suhua Li, John E. Moses |
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| Rok vydání: | 2018 |
| Předmět: |
Thionyl tetrafluoride
010405 organic chemistry chemistry.chemical_element General Medicine General Chemistry Imides 010402 general chemistry 01 natural sciences Combinatorial chemistry Sulfur Article Catalysis 0104 chemical sciences Fluorides Lactones chemistry.chemical_compound Sulfur fluoride chemistry Nucleophile Organometallic Compounds Click chemistry Reactivity (chemistry) Sulfones Fluoride |
| Zdroj: | Angewandte Chemie International Edition. 57:1939-1943 |
| ISSN: | 1433-7851 |
| DOI: | 10.1002/anie.201712145 |
| Popis: | Thionyl tetrafluoride (SOF4) is a valuable connective gas for sulfur fluoride exchange (SuFEx) click chemistry, that enables multidimensional linkages to be created via sulfur–oxygen (S–O) and sulfur–nitrogen (S–N) bonds. In this report, we expand the available SuFEx chemistry of SOF4 to include organolithium nucleophiles, and demonstrate, for the first time, the controlled projection of sulfur–carbon links at the sulfur center of SOF4-derived iminosulfur oxydifluorides (R1–N=SOF2). This protocol enables rapid and modular access to sulfonimidoyl fluorides [R1–N=SOFR2], another array of versatile SuFEx connectors with readily tunable reactivity of the S–F handle. Divergent connections derived from these valuable sulfonimidoyl fluoride units are also demonstrated, including the synthesis of sulfoximines, sulfonimidamides, and sulfonimidates. |
| Databáze: | OpenAIRE |
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