Gao, B., Li, S., Wu, P., Moses, J. E., Sharpless, K. B. (February 2018) SuFEx Chemistry of Thionyl Tetrafluoride (SOF(4) ) with Organolithium Nucleophiles: Synthesis of Sulfonimidoyl Fluorides, Sulfoximines, Sulfonimidamides, and Sulfonimidates. Angew Chem Int Ed Engl, 57 (7). pp. 1939-1943. ISSN 1433-7851 (Print)1433-7851
Abstract
Thionyl tetrafluoride (SOF(4) ) is a valuable connective gas for sulfur fluoride exchange (SuFEx) click chemistry that enables multidimensional linkages to be created via sulfur-oxygen and sulfur-nitrogen bonds. Herein, we expand the available SuFEx chemistry of SOF(4) to include organolithium nucleophiles, and demonstrate, for the first time, the controlled projection of sulfur-carbon links at the sulfur center of SOF(4) -derived iminosulfur oxydifluorides (R(1) -N=SOF(2) ). This method provides rapid and modular access to sulfonimidoyl fluorides (R(1) -N=SOFR(2) ), 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.
| Item Type: | Paper |
|---|---|
| Additional Information: | Angewandte Chemie (International ed. in English) |
| Subjects: | chemistry > techniques > click chemistry > Accelerated SuFEx Click Chemistry chemistry chemistry > techniques > click chemistry chemistry > techniques |
| CSHL Authors: | |
| Communities: | CSHL labs > Moses lab |
| Depositing User: | Matthew Dunn |
| Date: | 12 February 2018 |
| Date Deposited: | 08 Jan 2021 17:27 |
| Last Modified: | 20 Feb 2024 19:05 |
| PMCID: | PMC6005182 |
| URI: | https://repository.cshl.edu/id/eprint/39577 |
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