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A metal-free direct arene C-H amination

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The synthesis of aryl amines via the formation of a C−N bond is an essential tool for the preparation of functional materials, active pharmaceutical ingredients and bioactive products. Usually, this chemical connection is only possible by transition metal-catalyzed reactions, photochemistry or elect...

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Main Authors: Wang, Tao (Author) , Hoffmann, Marvin (Author) , Dreuw, Andreas (Author) , Hasagić, Edina (Author) , Hu, Chao (Author) , Stein, Philipp (Author) , Witzel, Sina (Author) , Shi, Hongwei (Author) , Yang, Yangyang (Author) , Rudolph, Matthias (Author) , Stuck, Fabian (Author) , Rominger, Frank (Author) , Kerscher, Marion (Author) , Comba, Peter (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: 05 March 2021
In: Advanced synthesis & catalysis
Year: 2021, Volume: 363, Issue: 11, Pages: 2783-2795
ISSN:1615-4169
DOI:10.1002/adsc.202100236
Online Access:Resolving-System, kostenfrei, Volltext: https://doi.org/10.1002/adsc.202100236
Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/adsc.202100236
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Author Notes:Tao Wang, Marvin Hoffmann, Andreas Dreuw, Edina Hasagić, Chao Hu, Philipp M. Stein, Sina Witzel, Hongwei Shi, Yangyang Yang, Matthias Rudolph, Fabian Stuck, Frank Rominger, Marion Kerscher, Peter Comba, and A. Stephen K. Hashmi
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Summary:The synthesis of aryl amines via the formation of a C−N bond is an essential tool for the preparation of functional materials, active pharmaceutical ingredients and bioactive products. Usually, this chemical connection is only possible by transition metal-catalyzed reactions, photochemistry or electrochemistry. Here, we report a metal-free arene C−H amination using hydroxylamine derivatives under benign conditions. A charge transfer interaction between the aminating reagents TsONHR and the arene substrates enables the chemoselective amination of the arene, even in the presence of various functional groups. Oxygen was crucial for an effective conversion and its accelerating role for the electron transfer step was proven experimentally. In addition, this was rationalized by a theoretical study which indicated the involvement of a dioxygen-bridged complex with a “Sandwich-like” arrangement of the aromatic starting materials and the aminating agents at the dioxygen molecule.
Item Description:Gesehen am 21.04.2021
Physical Description:Online Resource
ISSN:1615-4169
DOI:10.1002/adsc.202100236

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