Nickel‐Catalyzed N‐Arylation of NH‐Sulfoximines with Aryl Halides via Paired Electrolysis

A novel strategy for the N‐arylation of NH‐sulfoximines has been developed by merging nickel catalysis and electrochemistry (in an undivided cell), thereby providing a practical method for the construction of sulfoximine derivatives. Paired electrolysis is employed in this protocol, so a sacrificial...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2021-04, Vol.60 (17), p.9444-9449
Main Authors: Liu, Dong, Liu, Zhao‐Ran, Ma, Cong, Jiao, Ke‐Jin, Sun, Bing, Wei, Lei, Lefranc, Julien, Herbert, Simon, Mei, Tian‐Sheng
Format: Article
Language:English
Subjects:
Anodizing
arylation
Catalysis
Electrochemistry
Electrolysis
Functional groups
Halides
Ni catalysis
Nickel
organic electrochemistry
Oxidation
paired electrolysis
Room temperature
Sacrificial anodes
sulfoximines
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Summary:A novel strategy for the N‐arylation of NH‐sulfoximines has been developed by merging nickel catalysis and electrochemistry (in an undivided cell), thereby providing a practical method for the construction of sulfoximine derivatives. Paired electrolysis is employed in this protocol, so a sacrificial anode is not required. Owing to the mild reaction conditions, excellent functional group tolerance and yield are achieved. A preliminary mechanistic study indicates that the anodic oxidation of a NiII species is crucial to promote the reductive elimination of a C−N bond from the resulting NiIII species at room temperature. A novel strategy for the N‐arylation of NH‐sulfoximines has been developed by merging nickel catalysis and electrochemistry (in an undivided cell), thereby providing a practical method for the synthesis of sulfoximine derivatives. Paired electrolysis is employed in this protocol, so a sacrificial anode is not required.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202016310