期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 7, 页码 1939-1943出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201712145
关键词
click chemistry; organolithium reagents; SuFEx chemistry; sulfonimidoyl fluorides; thionyl tetrafluoride
资金
- NIH [P50 GM103368, R01 GM117145]
- Skaggs Institute for Chemical Biology
- Australian Research Council [FT170100156]
- Australian Research Council [FT170100156] Funding Source: Australian Research Council
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 and sulfur-nitrogen bonds. Herein, 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 (R-1-N=SOF2). This method provides rapid and modular access to sulfonimidoyl fluorides (R-1-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.
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