Petzold, Daniel and Singh, Pardeep and Almqvist, Fredrik and Koenig, Burkhard (2019) Visible-Light-Mediated Synthesis of beta-Chloro Ketones from Aryl Cyclopropanes. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 58 (25). pp. 8577-8580. ISSN 1433-7851, 1521-3773
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We report the visible-light-mediated synthesis of beta-chloro ketones from aryl cyclopropanes, oxygen, hydrochloric acid, and nitric acid. The operationally simple and catalyst-free method uses cheap standard laboratory reagents and displays broad functional-group tolerance. Moreover, scale up of the reaction and late-stage functionalization of bioactive compounds is possible, providing the opportunity to utilize the cyclopropane ring as a masked beta-chloro ketone in a reaction sequence. We propose a light-driven radical chain reaction initiated by the reaction of diluted hydrochloric and nitric acid to produce small quantities of molecular chlorine. The mechanistic hypothesis is supported by O-18 labelling and UV/Vis experiments, cyclovoltammetry, and several control reactions.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ARYLCYCLOPROPANE CATION RADICALS; 3-ELECTRON S(N)2 REACTIONS; PHOTOCHEMICAL ADDITION; DERIVATIVES; BIOGENESIS; STRATEGIES; INHIBITORS; PROBES; aryl cyclopropane; late-stage modification; photochemistry; radical chain reactions; beta-chloro ketones |
| 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: | 08 Apr 2020 06:56 |
| Last Modified: | 08 Apr 2020 06:56 |
| URI: | https://pred.uni-regensburg.de/id/eprint/26825 |
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