Quinazoline‐Assisted ortho‐Halogenation with N‐Halosuccinimides through Pd(II)‐Catalyzed C(sp2)−H Activation

An efficient quinazoline‐assisted ortho‐halogenation of 2‐arylquinazolines has been developed using N‐halosuccinimides as halogen sources with Pd(II)‐catalyzed C−H bond activation. No additional ligand and oxidant are required. This protocol is highly regioselective and applicable to a broad range o...

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Bibliographic Details
Published in:European journal of organic chemistry 2022-09, Vol.2022 (33), p.n/a
Main Authors: Wang, Yong, Wang, Hui, Yang, Qifan, Xie, Shihua, Zhu, Hongjun
Format: Article
Language:English
Subjects:
C−H activation
Experimentation
Functional groups
Halogenation
Heterocycle
Hydrogen bonds
Oxidizing agents
Palladium
Quinazoline
Substrates
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Summary:An efficient quinazoline‐assisted ortho‐halogenation of 2‐arylquinazolines has been developed using N‐halosuccinimides as halogen sources with Pd(II)‐catalyzed C−H bond activation. No additional ligand and oxidant are required. This protocol is highly regioselective and applicable to a broad range of quinazoline substrates bearing different functional groups, giving yields of up to 98 %. The mechanism of the quinazoline ortho‐halogenation was investigated by comprehensive experimentation. Herein, palladium(II)‐catalyzed halogenation of 2‐phenylquinazolines using N‐halosuccinimides as halogen sources was described via C−H activation under mild reaction conditions. A series of halogen‐substituted 2‐arylquinazolines were synthesized through C−H functionalization.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202200316