Visible-light-induced decarboxylative acylation of quinoxalin-2(1 <i>H</i>)-ones with α-oxo carboxylic acids under metal-, strong oxidant- and external photocatalyst-free conditions

Author(s): Long-Yong Xie ¹ ^, ² ^, ³ ^, ⁴ , You-Shu Bai ¹ ^, ² ^, ³ ^, ⁴ , Xiang-Qin Xu ¹ ^, ² ^, ³ ^, ⁴ , Xia Peng ¹ ^, ² ^, ³ ^, ⁴ , Hai-Shan Tang ¹ ^, ² ^, ³ ^, ⁴ , Ying Huang ⁵ ^, ⁶ ^, ⁷ ^, ⁴ , Ying-Wu Lin ⁸ ^, ⁹ ^, ¹⁰ ^, ⁴ , Zhong Cao ⁵ ^, ⁶ ^, ⁷ ^, ⁴ , Wei-Min He ¹ ^, ² ^, ³ ^, ⁴

Publication date (Electronic): 2020

Journal: Green Chemistry

Publisher: Royal Society of Chemistry (RSC)

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Abstract

An eco-friendly visible-light-induced decarboxylative acylation of quinoxalin-2(1 H)-ones and α-oxo carboxylic acids with air as the oxidant under external-photocatalyst-free conditions was established.

Abstract

A mild and eco-friendly visible-light-induced decarboxylative acylation of quinoxalin-2(1 H)-ones and α-oxo carboxylic acids with ambient air as the sole oxidant at room temperature was established. The reaction proceeded efficiently without any metal catalysts, strong oxidants or external-photosensitizers, ultimately reducing the generation of waste.

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Most cited references 88

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Metal-Free C(sp2)–H/N–H Cross-Dehydrogenative Coupling of Quinoxalinones with Aliphatic Amines under Visible-Light Photoredox Catalysis

Wei Wei, Leilei Wang, Pengli Bao … (2018)

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Visible-light-induced deoxygenative C2-sulfonylation of quinoline N -oxides with sulfinic acids

Long-Yong Xie, Tai-Gang Fang, Jia-Xi Tan … (2019)

The first example of direct synthesis of 2-sulfonylquinolines through visible-light-induced deoxygenative C2-sulfonylation of quinoline N -oxides with organic dye as the catalyst and ambient air as the sole oxidant was developed. The first example of visible-light-induced deoxygenative C2-sulfonylation of quinoline N -oxides with sulfinic acids in the presence of an organic dye as the catalyst was developed. The reaction conditions are eco-friendly and mild, employing ambient air as the sole oxidant and aqueous acetone solution as the solvent. This approach requires only a very low catalyst loading, allowing gram-scale preparation as well as late-stage modification of biologically active compounds bearing quinoline groups.

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Direct C–H Cyanoalkylation of Quinoxalin-2(1H)-ones via Radical C–C Bond Cleavage

Yu-Rui Gu, Li-Na Guo, Lin Yang … (2018)

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Author and article information

Contributors

Ying-Wu Lin: (View ORCID Profile)

Zhong Cao: (View ORCID Profile)

Wei-Min He: (View ORCID Profile)

Journal

Journal ID (publisher-id): GRCHFJ

Title: Green Chemistry

Abbreviated Title: Green Chem.

Publisher: Royal Society of Chemistry (RSC)

ISSN (Print): 1463-9262

ISSN (Electronic): 1463-9270

Publication date Created: March 9 2020

Publication date (Electronic): 2020

Volume: 22

Issue: 5

Pages: 1720-1725

Affiliations

[1 ]Department of Chemistry

[2 ]Hunan University of Science and Engineering

[3 ]Yongzhou 425100

[4 ]China

[5 ]Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation

[6 ]Changsha University of Science and Technology

[7 ]Changsha

[8 ]School of Chemistry and Chemical Engineering

[9 ]University of South China

[10 ]Hengyang 421001

Article

DOI: 10.1039/C9GC03899J

SO-VID: e589c9e7-dde8-43d9-ba1f-2a90a61bd230

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http://rsc.li/journals-terms-of-use

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