Journal
CHEMICAL SCIENCE
Volume 9, Issue 35, Pages 7115-7121Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8sc02547a
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Funding
- JSPS KAKENHI [15K17860]
- RIKEN
- JSPS Postdoctoral Fellowship [15F15340]
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We present a strategy for metal-free, alkene difunctionalization-type, oxy- and amino-perfluoroalkylations, using perfluoro acid anhydrides as practical and user-friendly perfluoroalkyl sources. This method provides efficient access to oxy-perfluoroalkylation products via carbocation formation due to the unique reactivity between styrenes and bis(perfluoroacyl) peroxides generated in situ from perfluoro acid anhydrides. This reaction is also applicable to metal-free intramolecular amino-perfluoroalkylation of styrenes bearing a pendant amino group. Synthetic utility of the oxy-trifluoromethylation products was confirmed by demonstrating derivatization via hydrolysis, elimination, and acid-catalyzed substitution with carbon nucleophiles. The mechanism of the carbocation formation was investigated experimentally and theoretically.
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