Photo- and Copper-Catalyzed Enantioselective Oxidation of Benzylic C(sp<sup>3</sup>)–H Bonds

Here, we report a photo- and copper-catalyzed enantioselective oxidation of benzylic C(sp<sup>3</sup>)-H bonds using <i>N</i>-hydroxyphthalimide as the oxygenated reagent. The reaction proceeds under mild conditions and does not require excess substrates or oxidants. The oxidation products can be readily transformed into chiral benzylic alcohols or hydroxylamines. Preliminary mechanism studies suggest that the oxidation reaction proceeds via a free radical mechanism.

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Publication Details

Journal
Journal of the American Chemical Society
Published
2025-05-26
DOI
https://doi.org/10.1021/jacs.5c04142
Citations
10
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
9.36
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article

Photo- and Copper-Catalyzed Enantioselective Oxidation of Benzylic C(sp3)–H Bonds

Ling Dai, Li‐Jun Xiao, Qi‐Lin Zhou, Jia‐Bin Pan et al.
10 citations
Journal of the American Chemical Society
Catalytic C–H Functionalization Methods
9.36
article

Photo- and Copper-Catalyzed Enantioselective Oxidation of Benzylic C(sp3)–H Bonds

Ling Dai, Li‐Jun Xiao, Qi‐Lin Zhou, Jia‐Bin Pan, Xianming Liu, Li Fu, Yin Yang, Chao Fan
article en
10 citations

Abstract

Here, we report a photo- and copper-catalyzed enantioselective oxidation of benzylic C(sp<sup>3</sup>)-H bonds using <i>N</i>-hydroxyphthalimide as the oxygenated reagent. The reaction proceeds under mild conditions and does not require excess substrates or oxidants. The oxidation products can be readily transformed into chiral benzylic alcohols or hydroxylamines. Preliminary mechanism studies suggest that the oxidation reaction proceeds via a free radical mechanism.

Journal of the American Chemical SocietyVol. 147(22)
Nankai University (CN)
Openalex Percentile: Top 2%
Catalytic C–H Functionalization Methods
9.36
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