Dual Photoredox/Copper-Catalyzed Radical <i>cis</i>-Selective Allylic Trifluoromethylation

We herein report a dual visible-light photoredox- and copper-catalyzed <i>Z</i>-selective allyl trifluoromethylation reaction of allylamine by using trifluoromethylpyridinium salt (TFSP) as the trifluoromethyl radical precursor. Various thermodynamically disfavorable allyl trifluoromethylated <i>cis</i>-enamides were accessible with moderate to good isolated yields. Cuprous oxide or copper nanoclusters were crucial as the co-catalyst for this transformation.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-05-19
DOI
https://doi.org/10.1021/acs.joc.5c00848
Citations
1
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.79

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article

Dual Photoredox/Copper-Catalyzed Radical cis-Selective Allylic Trifluoromethylation

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The Journal of Organic Chemistry
Fluorine in Organic Chemistry
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article

Dual Photoredox/Copper-Catalyzed Radical cis-Selective Allylic Trifluoromethylation

Shaoqun Zhu, Qiu Sun, Hong Hou, Xiao Yun Chen, Huaguang Yu, Changhao Yan, Ying Han, Yan Ren, Chengjun Chen, Xiaoyu Shen
article en
1 citations

Abstract

We herein report a dual visible-light photoredox- and copper-catalyzed <i>Z</i>-selective allyl trifluoromethylation reaction of allylamine by using trifluoromethylpyridinium salt (TFSP) as the trifluoromethyl radical precursor. Various thermodynamically disfavorable allyl trifluoromethylated <i>cis</i>-enamides were accessible with moderate to good isolated yields. Cuprous oxide or copper nanoclusters were crucial as the co-catalyst for this transformation.

The Journal of Organic ChemistryVol. 90(21)
Jianghan University (CN), Jiangsu University of Science and Technology (CN), Yangzhou University (CN)
National Natural Science Foundation of China
Openalex Percentile: Top 28%
Fluorine in Organic Chemistry
0.79
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