Electrochemical oxidation induced intermolecular aromatic C-H imidation

The dehydrogenative aryl C-H/N-H cross-coupling is a powerful synthetic methodology to install nitrogen functionalities into aromatic compounds. Herein, we report an electrochemical oxidation induced intermolecular cross-coupling between aromatics and sulfonimides with high regioselectivity through...

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Bibliographic Details
Published in:Nature communications 2019-11, Vol.10 (1), p.5467-10, Article 5467
Main Authors: Hu, Xia, Zhang, Guoting, Nie, Lei, Kong, Taige, Lei, Aiwen
Format: Article
Language:English
Subjects:
140/131
140/58
639/638/161/886
639/638/549/933
Acetic acid
Alkenes
Amines
Aniline
Anodizing
Aromatic compounds
Catalysts
Coupling (molecular)
Cross coupling
Dehydrogenation
Electrochemical oxidation
Electrochemistry
Electron transfer
Humanities and Social Sciences
multidisciplinary
Nitrogen
Oxidants
Oxidation
Oxidation process
Oxidizing agents
Regioselectivity
Science
Science (multidisciplinary)
Sulfonamides
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Summary:The dehydrogenative aryl C-H/N-H cross-coupling is a powerful synthetic methodology to install nitrogen functionalities into aromatic compounds. Herein, we report an electrochemical oxidation induced intermolecular cross-coupling between aromatics and sulfonimides with high regioselectivity through N -radical addition pathway under external-oxidant-free and catalyst-free conditions. A wide variety of arenes, heteroarenes, alkenes and sulfonimides are applicable scaffolds in this transformation. In addition, aryl sulfonamides or amines (aniline derivatives) can be obtained through different deprotection process. The cyclic voltammetry mechanistic study indicates that the N -centered imidyl radicals are generated via proton-coupled electron transfer event jointly mediated by tetrabutylammonium acetate and anode oxidation process. The dehydrogenative C-H/N-H cross-coupling serves to install nitrogen functionalities into arenes with the highest atom economy. Here, the authors report an electrochemical cross-coupling between aromatics and sulfonimides through an N-radical addition pathway under oxidant- and catalyst-free conditions.
ISSN:2041-1723
2041-1723
DOI:10.1038/s41467-019-13524-4