Citation: Zhonghua Qu, Pu Wang, Xing Chen, Guo-Jun Deng, Huawen Huang. Visible-light-driven Cadogan reaction[J]. Chinese Chemical Letters, ;2021, 32(8): 2582-2586. doi: 10.1016/j.cclet.2021.02.047 shu

Visible-light-driven Cadogan reaction

Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, China

hwhuang@xtu.edu.cn

Received Date: 3 January 2021
Revised Date: 21 February 2021
Accepted Date: 22 February 2021
Available Online: 25 February 2021

Figures(7)

Visible-light-driven photochemical Cadogan-type cyclization has been discovered. The organic D-A type photosensitizer 4CzIPN found to be an efficient mediator to transfer energy from photons to the transient intermediate that breaks the barriers of deoxygenation in Cadogan reaction and enables a mild metal-free access to carbazoles and related heterocycles. DFT calculation results indicate mildly endergonic formation of the intermediate complex of nitrobiarenes and PPh₃, which corresponds with experimental findings regarding reaction temperature. The robust synthetic capacity of the photoredox Cadogan reaction systems has been demonstrated by the viable productivity of a broad range of carbazoles and related N-heterocycles with good tolerance of various functionalities.
- Cadogan reaction,
- o-Nitrobiarene,
- Visible-light-driven,
- Deoxygenation,
- N-Heterocycles
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