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Amidinyl Radical Formation through Anodic N−H Bond Cleavage and Its Application in Aromatic C−H Bond Functionalization
Author(s) -
Zhao HuaiBo,
Hou ZhongWei,
Liu ZhanJiang,
Zhou ZeFeng,
Song Jinshuai,
Xu HaiChao
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201610715
Subject(s) - chemoselectivity , chemistry , radical , cleavage (geology) , reagent , bond cleavage , surface modification , substrate (aquarium) , nitrogen atom , combinatorial chemistry , medicinal chemistry , polymer chemistry , organic chemistry , catalysis , ring (chemistry) , materials science , oceanography , fracture (geology) , geology , composite material
We report herein an atom‐economical and sustainable approach to access amidinyl radical intermediates through the anodic cleavage of N−H bonds. The resulting nitrogen‐centered radicals undergo cyclizations with (hetero)arenes, followed by rearomatization, to afford functionalized tetracyclic benzimidazoles in a highly straightforward and efficient manner. This metal‐ and reagent‐free C−H/N−H cross‐coupling reaction exhibits a broad substrate scope and proceeds with high chemoselectivity.
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