Synthesis of 2-Arylquinolines from 2-Iodoanilines and β-Chloropropiophenones via Palladium-Catalyzed Cascade Reaction

Jooyeon Yoon; Cheol Hong Cheon

doi:10.1002/ajoc.201900290

Synthesis of 2-Arylquinolines from 2-Iodoanilines and β-Chloropropiophenones via Palladium-Catalyzed Cascade Reaction

Jooyeon Yoon, Cheol Hong Cheon^*

^*Corresponding author for this work

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

8 Citations (Scopus)

Abstract

A protocol to access 2-aryl-substituted quinolines from readily available 2-iodoanilines and β-chloropropiophenones, which are synthetic equivalents of acrylophenones, has been developed via the palladium-catalyzed cascade reaction. Various 2-iodoanilines and β-chloropropiophenones were applicable to this protocol to afford the desired quinoline products in good to high yields. Moreover, we demonstrated the usefulness of this protocol in direct synthesis of chloride-bridged dimeric iridium complexes, one of the key intermediates in the synthesis of iridium-based phosphorous materials, without the complete isolation of the quinolines.

Original language	English
Pages (from-to)	1631-1636
Number of pages	6
Journal	Asian Journal of Organic Chemistry
Volume	8
Issue number	9
DOIs	https://doi.org/10.1002/ajoc.201900290
Publication status	Published - 2019 Sept 1

Bibliographical note

Funding Information:
This work was supported by National Research Foundation of Korea (NRF) grants funded by the Korean Government (NRF-2018R1D1A1A02086110, NRF-2014-011165, Center for New Directions in Organic Synthesis).

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

Keywords

2-Arylquinolines
Cascade reaction
Ligand free
Palladium
β-Chloropropiophenone

ASJC Scopus subject areas

Organic Chemistry

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10.1002/ajoc.201900290

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title = "Synthesis of 2-Arylquinolines from 2-Iodoanilines and β-Chloropropiophenones via Palladium-Catalyzed Cascade Reaction",

abstract = "A protocol to access 2-aryl-substituted quinolines from readily available 2-iodoanilines and β-chloropropiophenones, which are synthetic equivalents of acrylophenones, has been developed via the palladium-catalyzed cascade reaction. Various 2-iodoanilines and β-chloropropiophenones were applicable to this protocol to afford the desired quinoline products in good to high yields. Moreover, we demonstrated the usefulness of this protocol in direct synthesis of chloride-bridged dimeric iridium complexes, one of the key intermediates in the synthesis of iridium-based phosphorous materials, without the complete isolation of the quinolines.",

keywords = "2-Arylquinolines, Cascade reaction, Ligand free, Palladium, β-Chloropropiophenone",

author = "Jooyeon Yoon and Cheon, \{Cheol Hong\}",

note = "Funding Information: This work was supported by National Research Foundation of Korea (NRF) grants funded by the Korean Government (NRF-2018R1D1A1A02086110, NRF-2014-011165, Center for New Directions in Organic Synthesis). Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

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doi = "10.1002/ajoc.201900290",

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T1 - Synthesis of 2-Arylquinolines from 2-Iodoanilines and β-Chloropropiophenones via Palladium-Catalyzed Cascade Reaction

AU - Yoon, Jooyeon

AU - Cheon, Cheol Hong

N1 - Funding Information: This work was supported by National Research Foundation of Korea (NRF) grants funded by the Korean Government (NRF-2018R1D1A1A02086110, NRF-2014-011165, Center for New Directions in Organic Synthesis). Publisher Copyright: © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2019/9/1

Y1 - 2019/9/1

N2 - A protocol to access 2-aryl-substituted quinolines from readily available 2-iodoanilines and β-chloropropiophenones, which are synthetic equivalents of acrylophenones, has been developed via the palladium-catalyzed cascade reaction. Various 2-iodoanilines and β-chloropropiophenones were applicable to this protocol to afford the desired quinoline products in good to high yields. Moreover, we demonstrated the usefulness of this protocol in direct synthesis of chloride-bridged dimeric iridium complexes, one of the key intermediates in the synthesis of iridium-based phosphorous materials, without the complete isolation of the quinolines.

AB - A protocol to access 2-aryl-substituted quinolines from readily available 2-iodoanilines and β-chloropropiophenones, which are synthetic equivalents of acrylophenones, has been developed via the palladium-catalyzed cascade reaction. Various 2-iodoanilines and β-chloropropiophenones were applicable to this protocol to afford the desired quinoline products in good to high yields. Moreover, we demonstrated the usefulness of this protocol in direct synthesis of chloride-bridged dimeric iridium complexes, one of the key intermediates in the synthesis of iridium-based phosphorous materials, without the complete isolation of the quinolines.

KW - 2-Arylquinolines

KW - Cascade reaction

KW - Ligand free

KW - Palladium

KW - β-Chloropropiophenone

UR - https://www.scopus.com/pages/publications/85067794616

U2 - 10.1002/ajoc.201900290

DO - 10.1002/ajoc.201900290

M3 - Article

AN - SCOPUS:85067794616

SN - 2193-5807

VL - 8

SP - 1631

EP - 1636

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 9

ER -

Synthesis of 2-Arylquinolines from 2-Iodoanilines and β-Chloropropiophenones via Palladium-Catalyzed Cascade Reaction

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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