Photocatalytic Cyclization Cascades by Radical Relay toward Pyrrolo[1,2‑a]indoles: Synthesis, Mechanism, and Application
A photocatalytic annulation cascade of unactivated N-alkene-linked indoles with Langlois’ reagent by a radical relay is developed at room temperature under blue LED irradiation. The reaction afforded a series of tri/difluoromethylated pyrrolo[1,2-a]indoles in moderate to good yields. The DFT study...
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| Veröffentlicht in: | Journal of organic chemistry 2024-03, Vol.89 (5), p.3509-3524 |
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| container_title | Journal of organic chemistry |
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| creator | He, Chen Wang, Qi Zhou, Xiaoyang Yi, Lin Zhang, Zhiqiang Zhang, Chun Xie, Haijiao Huang, Qitong Qiu, Guanyinsheng Yang, Min |
| description | A photocatalytic annulation cascade of unactivated N-alkene-linked indoles with Langlois’ reagent by a radical relay is developed at room temperature under blue LED irradiation. The reaction afforded a series of tri/difluoromethylated pyrrolo[1,2-a]indoles in moderate to good yields. The DFT study suggests that the reaction is ascribed to a rhodamine 6G-induced cyclization cascade involving vinyl addition-radical relay and hydrogen-atom-abstraction (HAA) processes, and interestingly, pyrrolo[1,2-a]indoles are applied as fluorescent dyes into the fluorescence spectrum and live-cell imaging. This paper represents an initial example on photocatalytic cyclization cascades by radical relay and the HAA process. |
| doi_str_mv | 10.1021/acs.joc.3c02959 |
| format | Article |
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| title | Photocatalytic Cyclization Cascades by Radical Relay toward Pyrrolo[1,2‑a]indoles: Synthesis, Mechanism, and Application |
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