Metal-Free Perfluoroarylation by Visible Light Photoredox Catalysis
| Authors | |
|---|---|
| Year of publication | 2016 |
| Type | Article in Periodical |
| Magazine / Source | ACS Catalysis |
| MU Faculty or unit | |
| Citation | |
| Web | http://pubs.acs.org/doi/abs/10.1021/acscatal.5b02410 |
| Doi | http://dx.doi.org/10.1021/acscatal.5b02410 |
| Field | Organic chemistry |
| Keywords | perfluorophenyl; photocatalysis; visible light; metal-free conditions; C-H arylation; transient spectroscopy |
| Description | 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. |
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