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Light and oxygen-enabled sodium trifluoromethanesulfinate-mediated selective oxidation of C–H bonds

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Abstract

Visible light-induced organic reactions are important chemical transformations in organic chemistry, and their efficiency highly depends on suitable photocatalysts. However, the commonly used photocatalysts are precious transition-metal complexes and elaborate organic dyes, which hamper large-scale production due to high cost. Here, for the first time, we report a novel strategy: light and oxygen-enabled sodium trifluoromethanesulfinate-mediated selective oxidation of C–H bonds, allowing high-value-added aromatic ketones and carboxylic acids to be easily prepared in high-to-excellent yields using readily available alkyl arenes, methyl arenes and aldehydes as materials. The mechanistic investigations showed that the treatment of inexpensive and readily available sodium trifluoromethanesulfinate with oxygen under irradiation of light could in situ form a pentacoordinate sulfide intermediate as an efficient photosensitizer. The method represents a highly efficient, economical and environmentally friendly strategy, and the light and oxygen-enabled sodium trifluoromethanesulfinate photocatalytic system represents a breakthrough in photochemistry.

Graphical abstract: Light and oxygen-enabled sodium trifluoromethanesulfinate-mediated selective oxidation of C–H bonds

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Article information


Submitted
31 Jan 2020
Accepted
29 May 2020
First published
29 May 2020

Green Chem., 2020, Advance Article
Article type
Paper

Light and oxygen-enabled sodium trifluoromethanesulfinate-mediated selective oxidation of C–H bonds

X. Zhu, Y. Liu, C. Liu, H. Yang and H. Fu, Green Chem., 2020, Advance Article , DOI: 10.1039/D0GC00383B

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