Synthesis of Polyaromatic Rings: Rh(III)-Catalyzed [5 + 1] Annulation of Enaminones with Vinyl Esters through C-H Bond Functionalization

Gaohui Liang; Jiaxin Rong; Wangbin Sun; Gengjia Chen; Yaojia Jiang; Teck Peng Loh

doi:10.1021/acs.orglett.8b03284

Synthesis of Polyaromatic Rings: Rh(III)-Catalyzed [5 + 1] Annulation of Enaminones with Vinyl Esters through C-H Bond Functionalization

Gaohui Liang, Jiaxin Rong, Wangbin Sun, Gengjia Chen, Yaojia Jiang^*, Teck Peng Loh

^*Corresponding author for this work

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

66 Citations (Scopus)

Abstract

An expedient [5 + 1] annulation method via Rh(III)-catalyzed C-H bond functionalization of enaminones to synthesize polyaromatic rings is described. The reaction tolerates a broad range of functional groups and offers a new entry to construct polycyclic aromatic compounds with amino and formyl substituents. A possible reaction mechanism was proposed based on the results obtained from isotope labeling experiments.

Original language	English
Pages (from-to)	7326-7331
Number of pages	6
Journal	Organic Letters
Volume	20
Issue number	22
DOIs	https://doi.org/10.1021/acs.orglett.8b03284
Publication status	Published - Nov 16 2018
Externally published	Yes

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Publisher Copyright:
Copyright © 2018 American Chemical Society.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "An expedient [5 + 1] annulation method via Rh(III)-catalyzed C-H bond functionalization of enaminones to synthesize polyaromatic rings is described. The reaction tolerates a broad range of functional groups and offers a new entry to construct polycyclic aromatic compounds with amino and formyl substituents. A possible reaction mechanism was proposed based on the results obtained from isotope labeling experiments.",

author = "Gaohui Liang and Jiaxin Rong and Wangbin Sun and Gengjia Chen and Yaojia Jiang and Loh, {Teck Peng}",

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year = "2018",

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doi = "10.1021/acs.orglett.8b03284",

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T2 - Rh(III)-Catalyzed [5 + 1] Annulation of Enaminones with Vinyl Esters through C-H Bond Functionalization

AU - Liang, Gaohui

AU - Rong, Jiaxin

AU - Sun, Wangbin

AU - Chen, Gengjia

AU - Jiang, Yaojia

AU - Loh, Teck Peng

PY - 2018/11/16

Y1 - 2018/11/16

N2 - An expedient [5 + 1] annulation method via Rh(III)-catalyzed C-H bond functionalization of enaminones to synthesize polyaromatic rings is described. The reaction tolerates a broad range of functional groups and offers a new entry to construct polycyclic aromatic compounds with amino and formyl substituents. A possible reaction mechanism was proposed based on the results obtained from isotope labeling experiments.

AB - An expedient [5 + 1] annulation method via Rh(III)-catalyzed C-H bond functionalization of enaminones to synthesize polyaromatic rings is described. The reaction tolerates a broad range of functional groups and offers a new entry to construct polycyclic aromatic compounds with amino and formyl substituents. A possible reaction mechanism was proposed based on the results obtained from isotope labeling experiments.

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Synthesis of Polyaromatic Rings: Rh(III)-Catalyzed [5 + 1] Annulation of Enaminones with Vinyl Esters through C-H Bond Functionalization

Abstract

Bibliographical note

ASJC Scopus Subject Areas

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