Issue 16, 2024

Selective C(sp3)–H bond aerobic oxidation enabled by a π-conjugated small molecule-oxygen charge transfer state

Abstract

Due to the high oxidation potential of arenes and alkenes, previous methods of benzylic and allylic C–H oxidation necessitated the use of strong oxidizing agents, metal catalysts, or free radical initiators (such as photocatalysts or hydrogen atom transfer reagents) to be effective. Herein, we employ oxygen to generate a triple-spin charge transfer state with π-conjugated compounds effectively accessing the triplet excited states of arenes, followed by energy transfer to form singlet oxygen facilitating C–H bond oxidation. Distinct from previous oxidations, it is the first time that a series of natural products and drug molecules (27 examples) are selectively oxidized without any catalysts or additives. The transformation can be implemented under sunlight to produce valuable unsaturated (aromatic) ketones and only water as waste, which meets every one of the 12 principles of green chemistry.

Graphical abstract: Selective C(sp3)–H bond aerobic oxidation enabled by a π-conjugated small molecule-oxygen charge transfer state

Supplementary files

Article information

Article type
Paper
Submitted
23 Apr 2024
Accepted
08 Jul 2024
First published
12 Jul 2024

Green Chem., 2024,26, 9241-9249

Selective C(sp3)–H bond aerobic oxidation enabled by a π-conjugated small molecule-oxygen charge transfer state

P. Huang, Y. Xu, H. Song, J. Wang, J. Wang, J. Li, B. Sun and C. Jin, Green Chem., 2024, 26, 9241 DOI: 10.1039/D4GC02010C

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