Chemistry - A European Journal · 2016 · 134 citations · 81 references
Natural SciencesChemistryMedicinal ChemistryCatalysisOrganic ChemistrySynthetic Medicinal ChemistryHeterocycle SynthesisHeterocyclic ChemistryPhotocatalysisPhotochemical SynthesisPhotochemistryRadical ReactionsHeterocycle FunctionalizationMild Reaction ConditionsPhotochemical FunctionalizationPhotoredox CatalysisPhotoredox FunctionalizationVisible-light Photocatalysis
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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Visible‐Light Photoredox Catalysis
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