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

Yong Wang; Hui Wang; Qifan Yang; Shihua Xie; Hongjun Zhu

doi:10.1002/ejoc.202200316

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

Yong Wang, Hui Wang, Qifan Yang, Shihua Xie, Hongjun Zhu

Nanjing Tech University

科研成果: 期刊稿件 › 文章 › 同行评审

2 引用（Scopus）

摘要

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.

源语言	英语
文章编号	e202200316
期刊	European Journal of Organic Chemistry
卷	2022
期	33
DOI	https://doi.org/10.1002/ejoc.202200316
出版状态	已出版 - 6 9月 2022

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title = "Quinazoline-Assisted ortho-Halogenation with N-Halosuccinimides through Pd(II)-Catalyzed C(sp2)−H Activation",

abstract = "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.",

keywords = "C−H activation, Halogenation, Heterocycle, Palladium, Quinazoline",

author = "Yong Wang and Hui Wang and Qifan Yang and Shihua Xie and Hongjun Zhu",

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year = "2022",

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T1 - Quinazoline-Assisted ortho-Halogenation with N-Halosuccinimides through Pd(II)-Catalyzed C(sp2)−H Activation

AU - Wang, Yong

AU - Wang, Hui

AU - Yang, Qifan

AU - Xie, Shihua

AU - Zhu, Hongjun

PY - 2022/9/6

Y1 - 2022/9/6

N2 - 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.

AB - 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.

KW - C−H activation

KW - Halogenation

KW - Heterocycle

KW - Palladium

KW - Quinazoline

UR - http://www.scopus.com/inward/record.url?scp=85129037080&partnerID=8YFLogxK

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DO - 10.1002/ejoc.202200316

M3 - 文章

AN - SCOPUS:85129037080

SN - 1434-193X

VL - 2022

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 33

M1 - e202200316

ER -

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

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