C–H chlorination of (hetero)anilines via photo/organo co-catalysis

Chlorinated (hetero)anilines are a class of important structural motifs that are widely present in synthetic building blocks and pharmaceuticals. Despite recent advancements, direct aniline chlorination still suffers from ortho / para and mono/poly chlorination selectivity problems. Herein, we discl...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2022-07, Vol.20 (26), p.5319-5324
Main Authors: Xie, Wuchen, Wang, Meng, Yang, Siyu, Chen, Yadong, Feng, Jie, Huang, Yatian
Format: Article
Language:English
Subjects:
Aniline
Catalysis
Chlorination
Selectivity
Substrates
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Summary:Chlorinated (hetero)anilines are a class of important structural motifs that are widely present in synthetic building blocks and pharmaceuticals. Despite recent advancements, direct aniline chlorination still suffers from ortho / para and mono/poly chlorination selectivity problems. Herein, we disclose a photo-redox and organo co-catalyzed chlorination method for anilines. This method has great substrate generality and excellent mono-chlorination selectivity. Another merit of this method is the late-stage modification of drug molecules, which would be useful in medicinal chemistry.
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob00834c