Meyer, Andreas U. and Slanina, Tomas and Yao, Chang-Jiang and Koenig, Burkhard (2016) Metal-Free Perfluoroarylation by Visible Light Photoredox Catalysis. ACS CATALYSIS, 6 (1). pp. 369-375. ISSN 2155-5435,
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Visible light and eosin Y catalyze the direct arylation of simple arenes with fluorinated aryl bromides by a photoredox process. The reaction scope is broad in fluorinated compounds and arenes and the general and simple procedure provides a metal-free alternative for the synthesis of synthetically valuable polyfluorinated biaryl structures. The mild reaction conditions allow a selective reaction with the alkaloid brucine without protection of functional groups illustrating the potential of the process for late stage functionalization. Mechanistic investigations reveal the photoreduction of eosin Y via its triplet state by triethylamine and subsequent electron transfer from the eosin Y radical anion to the polyfluorinated bromoarene, which fragments into the polyfluorinated aryl radical and a bromide anion. A radical chain reaction mechanism was excluded by a quenching factor analysis.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ELECTRON-DEFICIENT POLYFLUOROARENES; CROSS-COUPLING REACTIONS; ARYL DIAZONIUM SALTS; STRYCHNOS-NUX-VOMICA; C-H ARYLATION; EOSIN-Y; POTASSIUM POLYFLUOROBENZOATES; FLUORINATED AROMATICS; IPSO SUBSTITUTION; ORGANIC-SYNTHESIS; perfluorophenyl; photocatalysis; visible light; metal-free conditions; C-H arylation; transient spectroscopy |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 01 Mar 2019 12:36 |
| Last Modified: | 07 Mar 2019 10:12 |
| URI: | https://pred.uni-regensburg.de/id/eprint/2233 |
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