Carbene-Catalyzed Formal [3+3] Cycloaddition Reaction for Access to Substituted 2-Phenylbenzothiazoles

Zhibin Ni; Chengli Mou; Xun Zhu; Puying Qi; Song Yang; Yonggui Robin Chi; Zhichao Jin

doi:10.1002/ejoc.201901773

Carbene-Catalyzed Formal [3+3] Cycloaddition Reaction for Access to Substituted 2-Phenylbenzothiazoles

Zhibin Ni, Chengli Mou, Xun Zhu, Puying Qi, Song Yang, Yonggui Robin Chi, Zhichao Jin^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

A carbene-catalyzed oxidative cycloaddition reaction is developed for efficient access to multi-functionalized 2-phenylbenzothiazoles. A broad scope of heavily substituted arenes bearing 2-benzothiazole groups have been prepared in good to excellent yields. The remote C(sp²)–H bond in the substituted arene products can be activated by Pd catalysts in regio-selective fashion with the direction of the 2-benzothiazole groups.

Original language	English
Pages (from-to)	492-495
Number of pages	4
Journal	European Journal of Organic Chemistry
Volume	2020
Issue number	4
DOIs	https://doi.org/10.1002/ejoc.201901773
Publication status	Published - Jan 31 2020
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

ASJC Scopus Subject Areas

Physical and Theoretical Chemistry
Organic Chemistry

Keywords

2-Phenylbenzothiazoles
Benzene construction
Directing groups
N-heterocyclic carbene
Remote C(sp2–H) activation

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10.1002/ejoc.201901773

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title = "Carbene-Catalyzed Formal [3+3] Cycloaddition Reaction for Access to Substituted 2-Phenylbenzothiazoles",

abstract = "A carbene-catalyzed oxidative cycloaddition reaction is developed for efficient access to multi-functionalized 2-phenylbenzothiazoles. A broad scope of heavily substituted arenes bearing 2-benzothiazole groups have been prepared in good to excellent yields. The remote C(sp2)–H bond in the substituted arene products can be activated by Pd catalysts in regio-selective fashion with the direction of the 2-benzothiazole groups.",

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author = "Zhibin Ni and Chengli Mou and Xun Zhu and Puying Qi and Song Yang and Chi, {Yonggui Robin} and Zhichao Jin",

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T1 - Carbene-Catalyzed Formal [3+3] Cycloaddition Reaction for Access to Substituted 2-Phenylbenzothiazoles

AU - Ni, Zhibin

AU - Mou, Chengli

AU - Zhu, Xun

AU - Qi, Puying

AU - Yang, Song

AU - Chi, Yonggui Robin

AU - Jin, Zhichao

PY - 2020/1/31

Y1 - 2020/1/31

N2 - A carbene-catalyzed oxidative cycloaddition reaction is developed for efficient access to multi-functionalized 2-phenylbenzothiazoles. A broad scope of heavily substituted arenes bearing 2-benzothiazole groups have been prepared in good to excellent yields. The remote C(sp2)–H bond in the substituted arene products can be activated by Pd catalysts in regio-selective fashion with the direction of the 2-benzothiazole groups.

AB - A carbene-catalyzed oxidative cycloaddition reaction is developed for efficient access to multi-functionalized 2-phenylbenzothiazoles. A broad scope of heavily substituted arenes bearing 2-benzothiazole groups have been prepared in good to excellent yields. The remote C(sp2)–H bond in the substituted arene products can be activated by Pd catalysts in regio-selective fashion with the direction of the 2-benzothiazole groups.

KW - 2-Phenylbenzothiazoles

KW - Benzene construction

KW - Directing groups

KW - N-heterocyclic carbene

KW - Remote C(sp2–H) activation

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DO - 10.1002/ejoc.201901773

M3 - Article

AN - SCOPUS:85078060100

SN - 1434-193X

VL - 2020

SP - 492

EP - 495

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 4

ER -

Carbene-Catalyzed Formal [3+3] Cycloaddition Reaction for Access to Substituted 2-Phenylbenzothiazoles

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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