Quinone-Mediated Trifluoromethylation of Arenes and Heteroarenes with Visible Light

Bin Chang; Hongge Shao; Peng Yan; Wenzhao Qiu; Zhiqiang Weng; Rusheng Yuan

doi:10.1021/acssuschemeng.6b01682

Quinone-Mediated Trifluoromethylation of Arenes and Heteroarenes with Visible Light

Bin Chang, Hongge Shao, Peng Yan, Wenzhao Qiu, Zhiqiang Weng, Rusheng Yuan^*

^*Corresponding author for this work

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

37 Scopus citations

Abstract

The trifluoromethyl group can significantly influence the physical and chemical properties of organic molecules, thereby increasing their applications in the fields of pharmaceuticals, agrochemicals, and organic materials. An efficient visible-light-promoted method for the direct trifluoromethylation of arenes and heteroarenes has been developed using inexpensive CF₃SO₂Na as the CF₃ radical source and naturally ubiquitous quinones as oxidants. The regeneration of quinones was successfully realized by using a MnO₂-fixed bed. This operationally simple methodology not only provides an access to a wide variety of CF₃-containing building blocks from simple starting materials but also exhibits potential applications on a larger scale synthesis utilizing visible light energy.

Original language	English (US)
Pages (from-to)	334-341
Number of pages	8
Journal	ACS Sustainable Chemistry and Engineering
Volume	5
Issue number	1
DOIs	https://doi.org/10.1021/acssuschemeng.6b01682
State	Published - Jan 3 2017

Keywords

MnO
Photoinduced
Quinone
Radical
Trifluoromethylation

ASJC Scopus subject areas

General Chemistry
Environmental Chemistry
General Chemical Engineering
Renewable Energy, Sustainability and the Environment

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1021/acssuschemeng.6b01682

Cite this

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title = "Quinone-Mediated Trifluoromethylation of Arenes and Heteroarenes with Visible Light",

abstract = "The trifluoromethyl group can significantly influence the physical and chemical properties of organic molecules, thereby increasing their applications in the fields of pharmaceuticals, agrochemicals, and organic materials. An efficient visible-light-promoted method for the direct trifluoromethylation of arenes and heteroarenes has been developed using inexpensive CF3SO2Na as the CF3 radical source and naturally ubiquitous quinones as oxidants. The regeneration of quinones was successfully realized by using a MnO2-fixed bed. This operationally simple methodology not only provides an access to a wide variety of CF3-containing building blocks from simple starting materials but also exhibits potential applications on a larger scale synthesis utilizing visible light energy.",

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author = "Bin Chang and Hongge Shao and Peng Yan and Wenzhao Qiu and Zhiqiang Weng and Rusheng Yuan",

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doi = "10.1021/acssuschemeng.6b01682",

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AU - Chang, Bin

AU - Shao, Hongge

AU - Yan, Peng

AU - Qiu, Wenzhao

AU - Weng, Zhiqiang

AU - Yuan, Rusheng

PY - 2017/1/3

Y1 - 2017/1/3

N2 - The trifluoromethyl group can significantly influence the physical and chemical properties of organic molecules, thereby increasing their applications in the fields of pharmaceuticals, agrochemicals, and organic materials. An efficient visible-light-promoted method for the direct trifluoromethylation of arenes and heteroarenes has been developed using inexpensive CF3SO2Na as the CF3 radical source and naturally ubiquitous quinones as oxidants. The regeneration of quinones was successfully realized by using a MnO2-fixed bed. This operationally simple methodology not only provides an access to a wide variety of CF3-containing building blocks from simple starting materials but also exhibits potential applications on a larger scale synthesis utilizing visible light energy.

AB - The trifluoromethyl group can significantly influence the physical and chemical properties of organic molecules, thereby increasing their applications in the fields of pharmaceuticals, agrochemicals, and organic materials. An efficient visible-light-promoted method for the direct trifluoromethylation of arenes and heteroarenes has been developed using inexpensive CF3SO2Na as the CF3 radical source and naturally ubiquitous quinones as oxidants. The regeneration of quinones was successfully realized by using a MnO2-fixed bed. This operationally simple methodology not only provides an access to a wide variety of CF3-containing building blocks from simple starting materials but also exhibits potential applications on a larger scale synthesis utilizing visible light energy.

KW - MnO

KW - Photoinduced

KW - Quinone

KW - Radical

KW - Trifluoromethylation

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Quinone-Mediated Trifluoromethylation of Arenes and Heteroarenes with Visible Light

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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