Rackl, Daniel and Kais, Viktor and Kreitmeier, Peter and Reiser, Oliver (2014) Visible light photoredox-catalyzed deoxygenation of alcohols. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 10. pp. 2157-2165. ISSN 1860-5397,
Full text not available from this repository. (Request a copy)Abstract
Carbon-oxygen single bonds are ubiquitous in natural products whereas efficient methods for their reductive defunctionalization are rare. In this work an environmentally benign protocol for the activation of carbon-oxygen single bonds of alcohols towards a reductive bond cleavage under visible light photocatalysis was developed. Alcohols were activated as 3,5-bis(trifluoromethyl)-substituted benzoates and irradiation with blue light in the presence of [Ir(ppy)(2)(dtb-bpy)](PF6) as visible light photocatalyst and H nig's base as sacrificial electron donor in an acetonitrile/water mixture generally gave good to excellent yields of the desired defunctionalized compounds. Functional group tolerance is high but the protocol developed is limited to benzylic, alpha-carbonyl, and alpha-cyanoalcohols; with other alcohols a slow partial C-F bond reduction in the 3,5-bis(trifluoromethyl)benzoate moiety occurs.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ELECTRON-TRANSFER DEOXYGENATION; SECONDARY ALCOHOLS; C-O bond activation; deoxygenation; photochemistry; photoredox catalysis; visible light |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 14 Aug 2019 09:12 |
| Last Modified: | 14 Aug 2019 09:12 |
| URI: | https://pred.uni-regensburg.de/id/eprint/9560 |
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