Imine induced metal-free C–H arylation of indoles
Literature Information
Publication Date
2023-10-04
DOI
10.1039/D3QO01002C
Impact Factor
5.281
Authors
Lin Zhang, Jianan Gao, Bin Wang, Azhar Iqbal, Weiwei Jin, Yu Xia, Yonghong Zhang
View Original
Abstract
We report a metal-free and mild protocol for the direct arylation of indole at the C2 position using an imine transient directing group. Aryltriazenes are used as the aryl source with controllable activity, releasing the aryl radical and amine in a sustained manner under the action of a promoter. The transient imine directing groups were generated in situ by condensation of indole-3-carbaldehydes and the released amine to facilitate the direct C2 arylation of indoles via aryl radical addition with the assistance of transient unsaturated imine. This strategy is characterized by the absence of additional auxiliary groups, simple operation, and metal-free and mild reaction conditions, and provides insight into the metal-free direct arylation of indoles induced by in situ generated transient directing groups.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
N-Methyl-3-(1-naphthyloxy)-3-(2-thienyl)-1-propanamine hydrochloride (1:1)
CAS Number:
1188266-11-6
Molecular Formula:
C18H20ClNOS
![1-oxaspiro[4.4]nonan-6-one structure](https://static.chemtradehub.com/structs/134/134179-01-4-e051.webp "1-oxaspiro[4.4]nonan-6-one structure")
![1-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-benzo[d]imidazol-2(3H)-one structure](https://static.chemtradehub.com/structs/603/60373-71-9-7dfb.webp "1-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-benzo[d]imidazol-2(3H)-one structure")
1-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-benzo[d]imidazol-2(3H)-one
CAS Number:
60373-71-9
Molecular Formula:
C19H19N3O
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