Visible light-mediated selective α-functionalization of 1,3-dicarbonyl compounds via disulfide induced aerobic oxidation

Jingnan Zhao; Fan Yang; Zongyi Yu; Xiaofei Tang; Yufeng Wu; Cunfei Ma; Qingwei Meng

doi:10.1039/C9CC06544J

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Visible light-mediated selective α-functionalization of 1,3-dicarbonyl compounds via disulfide induced aerobic oxidation†

Jingnan Zhao,^a Fan Yang,^a Zongyi Yu,^a Xiaofei Tang,^a Yufeng Wu,^a Cunfei Ma^a and Qingwei Meng

*^a

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* Corresponding authors

^a State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology, Dalian, P. R. China
E-mail: mengqw@dlut.edu.cn

Abstract

A visible light-mediated α-functionalization of 1,3-dicarbonyl compounds with switchable selectivity induced by disulfide is disclosed. Upon irradiation with visible light, the metal- and base-free α-hydroxylation or α-hydroxymethylation reaction proceeded smoothly through a disulfide-catalyzed oxidation under mild conditions. The combination of a continuous-flow strategy could further improve the reaction efficiencies.

This article is part of the themed collection: Editor’s Choice: Main group reagents and catalysts in organic reactions

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Article information

DOI: https://doi.org/10.1039/C9CC06544J
Article type: Communication
Submitted: 23 Aug 2019
Accepted: 07 Oct 2019
First published: 07 Oct 2019

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Chem. Commun., 2019,55, 13008-13011

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Visible light-mediated selective α-functionalization of 1,3-dicarbonyl compounds via disulfide induced aerobic oxidation

J. Zhao, F. Yang, Z. Yu, X. Tang, Y. Wu, C. Ma and Q. Meng, Chem. Commun., 2019, 55, 13008 DOI: 10.1039/C9CC06544J

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Chemical Communications

Visible light-mediated selective α-functionalization of 1,3-dicarbonyl compounds via disulfide induced aerobic oxidation†

Abstract

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Visible light-mediated selective α-functionalization of 1,3-dicarbonyl compounds via disulfide induced aerobic oxidation

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