Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 2, Pages 656-659Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201409473
Keywords
aldehydes; enolates; fluorine; N-heterocyclic carbenes; oxidation
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Funding
- Tsinghua University
- Thousand Plan Youth program of China
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Described is the first study on oxidative enantioselective -fluorination of simple aliphatic aldehydes enabled by N-heterocyclic carbene catalysis. N-fluorobis(phenyl)sulfonimide serves as a an oxidant and as an F source. The CF bond formation occurs directly at the position of simple aliphatic aldehydes, thus overcoming nontrivial challenges, such as competitive difluorination and nonfluorination, and proceeds with high to excellent enantioselectivities.
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