Regioselective Synthesis of Polycyclic and Heptagon-embedded Aromatic Compounds through a Versatile π-Extension of Aryl Halides

Wai Chung Fu; Zheng Wang; Wesley Ting Kwok Chan; Zhenyang Lin; Fuk Yee Kwong

doi:10.1002/anie.201703551

Regioselective Synthesis of Polycyclic and Heptagon-embedded Aromatic Compounds through a Versatile π-Extension of Aryl Halides

Wai Chung Fu, Zheng Wang, Wesley Ting Kwok Chan, Zhenyang Lin, Fuk Yee Kwong

The Hong Kong Polytechnic University

Research output: Journal article publication › Journal article › Academic research › peer-review

116 Citations (Scopus)

Abstract

A versatile π-extension reaction was developed based on the three-component cross-coupling of aryl halides, 2-haloarylcarboxylic acids, and norbornadiene. The transformation is driven by the direction and subsequent decarboxylation of the carboxyl group, while norbornadiene serves as an ortho-C−H activator and ethylene synthon via a retro-Diels–Alder reaction. Comprehensive DFT calculations were performed to account for the catalytic intermediates.

Original language	English
Pages (from-to)	7166-7170
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	25
DOIs	https://doi.org/10.1002/anie.201703551
Publication status	Published - 12 Jun 2017

Keywords

cross-coupling
C−H functionalization
decarboxylation
palladium
polycyclic aromatic hydrocarbons

ASJC Scopus subject areas

Catalysis
General Chemistry

More information

10.1002/anie.201703551

http://hdl.handle.net/10397/95307

Cite this

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title = "Regioselective Synthesis of Polycyclic and Heptagon-embedded Aromatic Compounds through a Versatile π-Extension of Aryl Halides",

abstract = "A versatile π-extension reaction was developed based on the three-component cross-coupling of aryl halides, 2-haloarylcarboxylic acids, and norbornadiene. The transformation is driven by the direction and subsequent decarboxylation of the carboxyl group, while norbornadiene serves as an ortho-C−H activator and ethylene synthon via a retro-Diels–Alder reaction. Comprehensive DFT calculations were performed to account for the catalytic intermediates.",

keywords = "cross-coupling, C−H functionalization, decarboxylation, palladium, polycyclic aromatic hydrocarbons",

author = "Fu, {Wai Chung} and Zheng Wang and Chan, {Wesley Ting Kwok} and Zhenyang Lin and Kwong, {Fuk Yee}",

note = "Funding Information: We thank RGC of Hong Kong (CRF: C5023-14G, GRF: 15336716 and PolyU11/CRF/13E) for financial and X-ray equipment support; and Prof. Gavin C. Tsui (CUHK) and Prof. Man-Kit Leung (NTU, Taiwan) for helpful discussions to this manuscript. Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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doi = "10.1002/anie.201703551",

language = "English",

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journal = "Angewandte Chemie - International Edition",

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Regioselective Synthesis of Polycyclic and Heptagon-embedded Aromatic Compounds through a Versatile π-Extension of Aryl Halides. / Fu, Wai Chung; Wang, Zheng; Chan, Wesley Ting Kwok et al.
In: Angewandte Chemie - International Edition, Vol. 56, No. 25, 12.06.2017, p. 7166-7170.

Research output: Journal article publication › Journal article › Academic research › peer-review

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AU - Fu, Wai Chung

AU - Wang, Zheng

AU - Chan, Wesley Ting Kwok

AU - Lin, Zhenyang

AU - Kwong, Fuk Yee

N1 - Funding Information: We thank RGC of Hong Kong (CRF: C5023-14G, GRF: 15336716 and PolyU11/CRF/13E) for financial and X-ray equipment support; and Prof. Gavin C. Tsui (CUHK) and Prof. Man-Kit Leung (NTU, Taiwan) for helpful discussions to this manuscript. Publisher Copyright: © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2017/6/12

Y1 - 2017/6/12

N2 - A versatile π-extension reaction was developed based on the three-component cross-coupling of aryl halides, 2-haloarylcarboxylic acids, and norbornadiene. The transformation is driven by the direction and subsequent decarboxylation of the carboxyl group, while norbornadiene serves as an ortho-C−H activator and ethylene synthon via a retro-Diels–Alder reaction. Comprehensive DFT calculations were performed to account for the catalytic intermediates.

AB - A versatile π-extension reaction was developed based on the three-component cross-coupling of aryl halides, 2-haloarylcarboxylic acids, and norbornadiene. The transformation is driven by the direction and subsequent decarboxylation of the carboxyl group, while norbornadiene serves as an ortho-C−H activator and ethylene synthon via a retro-Diels–Alder reaction. Comprehensive DFT calculations were performed to account for the catalytic intermediates.

KW - cross-coupling

KW - C−H functionalization

KW - decarboxylation

KW - palladium

KW - polycyclic aromatic hydrocarbons

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JO - Angewandte Chemie - International Edition

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Regioselective Synthesis of Polycyclic and Heptagon-embedded Aromatic Compounds through a Versatile π-Extension of Aryl Halides

Abstract

Keywords

ASJC Scopus subject areas

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