Journal
ORGANIC LETTERS
Volume 16, Issue 17, Pages 4524-4527Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol502071g
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- SERB, India [SR/S1/IC-24/2011]
- CSIR-India
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Regioselective addition across the alkynes has been achieved in a silver-catalyzed protocol utilizing Langlois reagent (CF3SO2Na) and molecular O-2 to access medicinally active alpha-trifluoromethyl ketone compounds. This method was successful in producing alpha-trifluoromethyl ketone in heterocyclic scaffolds, which are incompatible with earlier strategies. Experimental findings suggest a mechanism involving alpha-styrenyl radical intermediate and 1-methyl-2-pyrroliclinone (NMP) solvent, which leads to crystallographically characterized N-methylsuccinimide. Isotope labeling, kinetic studies, and intermediate trapping further helped to gain insight into this energy-demanding process.
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