Visible-light-initiated nickel-catalyzed amination of aryl halides using thioxanthen-9-one as a photocatalyst

This paper describes a mild strategy for amination of aryl halides with anilines by dual photoredox and nickel catalysis. Inexpensive and commercially available thioxanthen-9-one significantly accelerated this cross-coupling, providing a diverse range of diarylamines in good yields (41–93%) at room...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2023-07, Vol.10 (14), p.3612-3618
Main Authors: Da-Liang, Zhu, Li, Jie, Young, David James, Wang, Yanqing, Hong-Xi, Li
Format: Article
Language:English
Subjects:
Amination
Aniline
Aromatic compounds
Catalysis
Chemical synthesis
Coupling (molecular)
Cross coupling
Energy transfer
Fluorescent lamps
Functional groups
Halides
Natural products
Nickel
Organic chemistry
Room temperature
Scale (corrosion)
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Summary:This paper describes a mild strategy for amination of aryl halides with anilines by dual photoredox and nickel catalysis. Inexpensive and commercially available thioxanthen-9-one significantly accelerated this cross-coupling, providing a diverse range of diarylamines in good yields (41–93%) at room temperature. This reaction proceeded under compact fluorescent lamp light or sunlight and was tolerant of a wide range of functional groups. It was applied to the synthesis of natural product and drug molecules, and proceeded efficiently on a gram-scale. The mechanism involves oxidative addition of an aryl halide to nickel(0), transmetalation of aryl-Ni(ii) halide, energy transfer from triplet photosensitizer thioxanthen-9-one to an aryl-Ni(ii)-amino intermediate, and subsequent reductive elimination to diarylamine.
ISSN:2052-4110
2052-4110
DOI:10.1039/d3qo00545c