Foell, Thomas and Rehbein, Julia and Reiser, Oliver (2018) Ir(ppy)(3)-Catalyzed, Visible-Light-Mediated Reaction of alpha-Chloro Cinnamates with Enol Acetates: An Apparent Halogen Paradox. ORGANIC LETTERS, 20 (18). pp. 5794-5798. ISSN 1523-7060, 1523-7052
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The visible-light-mediated activation of vinyl chlorides derived from alpha-chloro ethyl cinnamates via oxidative quenching of excited photocatalyst fac-Ir(ppy)(3) is described. Upon photoelectron transfer and chloride extrusion, the corresponding vinyl radical can be efficiently trapped by enol acetates, giving rise to synthetically useful 1,4-dicarbonyl compounds in good to excellent yields. This transformation is distinguished by mild and environmentally benign reaction conditions and can be performed on a multigram scale, in sharp contrast to contrasting alpha-bromo ethyl cinnamates, which show low conversion under the various conditions applied.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | PHOTOREDOX CATALYSIS; ELECTRON-TRANSFER; HECK REACTION; REDUCTION; BROMOCHALCONES; HETEROARENES; TRANSITION; GENERATION; ARYLATION; RADICALS; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 12 Dec 2019 14:03 |
| Last Modified: | 12 Dec 2019 14:03 |
| URI: | https://pred.uni-regensburg.de/id/eprint/13839 |
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