Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 13, Pages 4395-4399Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201600190
Keywords
halides; photocatalysis; synthetic methods; trifluoromethylthiolation; visible light
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Funding
- Deutsche Forschungsgemeinschaft
- Fonds der Chemischen Industrie
- Alexander von Humboldt Foundation
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Herein, we report a new visible-light-promoted strategy to access radical trifluoromethylthiolation reactions by combining halide and photoredox catalysis. This approach allows for the synthesis of vinyl-SCF3 compounds of relevance in pharmaceutical chemistry directly from alkenes under mild conditions with irradiation from household light sources. Furthermore, alkyl-SCF3-containing cyclic ketone and oxindole derivatives can be accessed by radical-polar crossover semi-pinacol and cyclization processes. Inexpensive halide salts play a crucial role in activating the trifluoromethylthiolating reagent towards photoredox catalysis and aid the formation of the SCF3 radical.
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