期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 60, 期 48, 页码 25477-25484出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202111006
关键词
charge transfer complexes; fluoromethyl radicals; phosphonium salts; photolysis; sigma-hole effect
资金
- National Natural Science Foundation of China [22001248, 21773240]
- China Postdoctoral Science Foundation [119103S309]
- Fundamental Research Funds for the Central Universities
- University of the Chinese Academy of Sciences
The sigma-hole effect is utilized to facilitate the photolysis of phosphonium iodide salts, selectively generating fluoromethyl radicals, allowing for mono-, di-, and trifluoromethylation reactions using fluoromethylphosphonium salts.
The sigma (sigma)-hole effect has emerged as a promising tool to construct novel architectures endowed with new properties. A simple yet effective strategy for the generation of monofluoromethyl radicals is a continuing challenge within the synthetic community. Fluoromethylphosphonium salts are easily available, air- and thermally stable, as well as simple-to-handle. Herein, we report the ability of the sigma-hole effect to facilitate the visible-light-triggered photolysis of phosphonium iodide salts, a charge-transfer complex, selectively giving fluoromethyl radicals. The usefulness and versatility of this new protocol are demonstrated through the mono-, di-, and trifluoromethylation of a variety of alkenes.
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