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Issue 6, 2020
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Visible-light induced disproportionation of pyrrole derivatives for photocatalyst-free aryl halides reduction

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Abstract

As a green synthetic approach, visible light-driven photosynthesis is highly desirable in arylation of inert alkyl halides, as they are important precursors in the total synthesis of natural products and pharmaceuticals. However, the high bond dissociation energy of aryl halides is typically out of the range of a single visible-light photon. Here, we propose an essential initiation and subsequent electron-transfer step process for visible light-driven aryl halide reduction, and identify the key pyrrole radical anion intermediate, that acts as the strong reduction species. We propose a photoinduced disproportionation (PDP) approach without the addition of any photocatalysts or additives to afford radical anions of pyrrole derivatives, which have enough reduction power to transfer an electron to aryl halide, giving rise to the corresponding aryl radical to afford the desired C–H arylated heterocyclic product. Once generated, the heterocyclic product can undergo the same photoinduced disproportionation (PDP) process to activate aryl halides, thereby promoting the reaction rate. This unprecedented initiation step, which was carried out in the absence of photocatalysts and additives under ambient conditions, can also be used for coupling a wide range of (hetero)aryl halides and pyrrole derivatives, as well as the synthesis of drug intermediates and biorelevant compounds.

Graphical abstract: Visible-light induced disproportionation of pyrrole derivatives for photocatalyst-free aryl halides reduction

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Supplementary files

Article information


Submitted
12 Dec 2019
Accepted
17 Feb 2020
First published
18 Feb 2020

Green Chem., 2020,22, 1911-1918
Article type
Paper

Visible-light induced disproportionation of pyrrole derivatives for photocatalyst-free aryl halides reduction

Z. Li, S. Li, E. Hofman, A. Hunter Davis, G. Leem and W. Zheng, Green Chem., 2020, 22, 1911 DOI: 10.1039/C9GC04248B

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