Rhodium-Catalyzed Aromatic C–H Allylation with α,β-Unsaturated Imines

Reaction of 2-arylpyridines with α,β-unsaturated imines in the presence of 2.5 mol % of [Cp*RhCl<sub>2</sub>]<sub>2</sub> and 10 mol % of AgSbF<sub>6</sub> in acetone affords allylated 2-arylpyridines with an enamine unit located in the allyl segment. This method features <i>ortho</i>-monoallylation selectivity and <i>Z</i>-selectivity of the C-C double bonds, is applicable to a wide range of substrates, and is compatible with air and functional groups such as halides, CF<sub>3</sub>, COOMe, OH, MeO, and ketal groups.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-05-14
DOI
https://doi.org/10.1021/acs.joc.5c00484
Citations
1
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.94

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article

Rhodium-Catalyzed Aromatic C–H Allylation with α,β-Unsaturated Imines

Weitao Hu, Zhong‐Xia Wang
1 citations
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
0.94
article

Rhodium-Catalyzed Aromatic C–H Allylation with α,β-Unsaturated Imines

Weitao Hu, Zhong‐Xia Wang
article en
1 citations

Abstract

Reaction of 2-arylpyridines with α,β-unsaturated imines in the presence of 2.5 mol % of [Cp*RhCl<sub>2</sub>]<sub>2</sub> and 10 mol % of AgSbF<sub>6</sub> in acetone affords allylated 2-arylpyridines with an enamine unit located in the allyl segment. This method features <i>ortho</i>-monoallylation selectivity and <i>Z</i>-selectivity of the C-C double bonds, is applicable to a wide range of substrates, and is compatible with air and functional groups such as halides, CF<sub>3</sub>, COOMe, OH, MeO, and ketal groups.

The Journal of Organic ChemistryVol. 90(20)
University of Science and Technology of China (CN)
National Natural Science Foundation of China
Openalex Percentile: Top 26%
Catalytic C–H Functionalization Methods
0.94
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