Herein, we report a photocatalytic procedure that enables the acylation/arylation of unfunctionalized alkyl derivatives in flow. The method exploits the ability of the decatungstate anion to act as a hydrogen atom abstractor and produce nucleophilic carbon-centered radicals that are intercepted by a nickel catalyst to ultimately forge C(sp3)−C(sp2) bonds. Owing to the intensified conditions in flow, the reaction time can be reduced from 12–48 hours to only 5–15 minutes. Finally, kinetic measurements highlight how the intensified conditions do not change the reaction mechanism but reliably speed up the overall process.
Mazzarella, D., Pulcinella, A., Bovy, L., Broersma, R., Noël, T. (2021). Rapid and Direct Photocatalytic C(sp3)−H Acylation and Arylation in Flow. ANGEWANDTE CHEMIE. INTERNATIONAL EDITION, 60(39), 21277-21282 [10.1002/anie.202108987].
Rapid and Direct Photocatalytic C(sp3)−H Acylation and Arylation in Flow
Daniele Mazzarella;
2021-01-01
Abstract
Herein, we report a photocatalytic procedure that enables the acylation/arylation of unfunctionalized alkyl derivatives in flow. The method exploits the ability of the decatungstate anion to act as a hydrogen atom abstractor and produce nucleophilic carbon-centered radicals that are intercepted by a nickel catalyst to ultimately forge C(sp3)−C(sp2) bonds. Owing to the intensified conditions in flow, the reaction time can be reduced from 12–48 hours to only 5–15 minutes. Finally, kinetic measurements highlight how the intensified conditions do not change the reaction mechanism but reliably speed up the overall process.| File | Dimensione | Formato | |
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Angew Chem Int Ed - 2021 - Mazzarella - Rapid and Direct Photocatalytic C sp3 H Acylation and Arylation in Flow.pdf
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