Giedyk, Maciej and Narobe, Rok and Weiss, Sophia and Touraud, Didier and Kunz, Werner and Koenig, Burkhard (2020) Photocatalytic activation of alkyl chlorides by assembly-promoted single electron transfer in microheterogeneous solutions. NATURE CATALYSIS, 3 (1). pp. 40-47. ISSN 2520-1158,
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Photocatalytic activation of alkyl carbon-chlorine bonds has constantly proven difficult due to the high energies needed to cleave this stable bond. Here a surfactant-based photocatalytic system is used, allowing for the radical dehalogenation and subsequent reactivity of unactivated alkyl chlorides. Photoredox catalysis has developed into a powerful tool for the synthesis of organic compounds with diverse structures. However, stable carbon-chloride bonds remain beyond the energetic limits of the outer-sphere photoreductive activation. Here, we demonstrate that the organization of the reacting species in microstructured, aqueous solutions allows generation of carbon-centred radicals from non-activated alkyl chlorides in the presence of double bonds via assembly-promoted single electron transfer. Photocatalytic systems consisting of a surfactant, organic substrates and additives have been designed, characterized and applied for radical dechlorination, addition and cyclization reactions. Cheap and commercially available blue light-emitting diodes are used as the irradiation source for the transformations. Mechanistic studies indicate the accumulation of the energy of two visible light photons in one catalytic cycle.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | HYDRATED ELECTRONS; RADICAL REACTIONS; UNACTIVATED ALKYL; UP-CONVERSION; ARYL HALIDES; REDUCTION; PHOTOSENSITIZER; MICROEMULSION; POTENTIALS; CATALYSTS; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König Chemistry and Pharmacy > Institut für Physikalische und Theoretische Chemie Chemistry and Pharmacy > Institut für Physikalische und Theoretische Chemie > Chair of Chemistry VI - Physical Chemistry (Solution Chemistry) Chemistry and Pharmacy > Institut für Physikalische und Theoretische Chemie > Chair of Chemistry VI - Physical Chemistry (Solution Chemistry) > Prof. Dr. Werner Kunz |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 08 Apr 2021 08:38 |
| Last Modified: | 08 Apr 2021 08:38 |
| URI: | https://pred.uni-regensburg.de/id/eprint/45537 |
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