Eisenhofer, Anna and Hioe, Johnny and Gschwind, Ruth M. and Koenig, Burkhard (2017) Photocatalytic Phenol-Arene C-C and C-O Cross-Dehydrogenative Coupling. WILEY-V C H VERLAG GMBH, WEINHEIM.
Full text not available from this repository. (Request a copy)Abstract
Phenol-containing nonsymmetrical biaryls play an important role in natural-product synthesis, as ligands in metal catalysis, and in organic functional materials. Their synthesis through cross-coupling reactions by two-fold direct C-H activation are important and challenging transformations. In the last decade, a variety of useful oxidative methods have been developed. The key to efficiency and selectivity typically is the application of highly fluorinated solvent systems. Herein, we describe the visible-light-mediated C-C and C-O cross-coupling of electron-rich phenols and arenes by using [Ru(bpz)(3)](PF6)(2)] as photocatalyst and ammonium persulfate as terminal oxidant. The method requires no leaving group functionalities, which allows the use of simple activated arenes as starting materials. Furthermore, the approach features good chemo- and regioselectivity as well as functional group tolerance, even upon the replacement of fluoro alcohols by acetonitrile. The selectivity for the formation of nonsymmetrical biaryls is rationalized on the basis of the nucleophilicity N values and the oxidation potentials E-ox of the electron-rich substrates.
| Item Type: | Other |
|---|---|
| Uncontrolled Keywords: | ELECTRON-TRANSFER PROCESSES; CATALYZED DIRECT ARYLATION; BIARYL NATURAL-PRODUCTS; ARYL BOND FORMATION; PHOTOREDOX CATALYSIS; REDOX POTENTIALS; METAL-FREE; SUBSTITUTED 2-NAPHTHOLS; ORGANIC-SYNTHESIS; EXCITED-STATE; Cross-coupling; Photocatalysis; Phenols; Biaryls; C-O coupling; Arenes |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Prof. Dr. Ruth Gschwind |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 14 Dec 2018 13:10 |
| Last Modified: | 11 Feb 2019 14:06 |
| URI: | https://pred.uni-regensburg.de/id/eprint/1030 |
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