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Journal Article

Visible-light-driven photochemical activation of sp3 C-H bond for hemiaminal formation

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Li,  Lina
Aleksandr Savateev, Kolloidchemie, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Zhang,  Guigang
Aleksandr Savateev, Kolloidchemie, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Savateev,  Aleksandr
Aleksandr Savateev, Kolloidchemie, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Kurpil,  Bogdan
Aleksandr Savateev, Kolloidchemie, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Antonietti,  Markus
Markus Antonietti, Kolloidchemie, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Zhao,  Yubao
Aleksandr Savateev, Kolloidchemie, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Citation

Li, L., Zhang, G., Savateev, A., Kurpil, B., Antonietti, M., & Zhao, Y. (2018). Visible-light-driven photochemical activation of sp3 C-H bond for hemiaminal formation. Asian Journal of Organic Chemistry, 7(12), 2464-2467. doi:10.1002/ajoc.201800653.


Cite as: https://hdl.handle.net/21.11116/0000-0002-85F6-2
Abstract
Photochemical synthesis of organic chemicals has attracted a massive revitalized research interest. A metal-free photochemical system with carbon tetrabromide (CBr4) is here developed for the synthesis of hemiaminal compounds. In this reaction system, the sp3 C-H bond of the N-alkyl group in the amide is photochemically activated, producing an ionic iminium species. The hemiaminal compounds are produced by nucleophilic attack of the iminium ion by alcohol in the presence of base. This photochemical conversion system shows high yield and broad substrate scope.