Palladium-Catalyzed Domino Carboetherification Reactions: Synthesis of Bis-Heterocycles Bearing Isoxazoline and Methyleneindole Motifs

A novel and highly efficient Pd-catalyzed approach for the synthesis of bis-heterocycles featuring both isoxazoline and methyleneindole motifs is demonstrated. The in situ formation of vinyl Pd(II) species through an alkyne-tethered carbamoyl chloride cyclization is crucial, and the innovative Pd-catalyzed carboetherification of β,γ-unsaturated oximes with vinyl Pd(II) species has been developed. This method is not only operationally straightforward but also exhibits a broad substrate scope and excellent functional group tolerance.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-12-18
DOI
https://doi.org/10.1021/acs.joc.4c02679
Citations
5
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
1.25

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article

Palladium-Catalyzed Domino Carboetherification Reactions: Synthesis of Bis-Heterocycles Bearing Isoxazoline and Methyleneindole Motifs

Shuaijie Wu, Youzhou He, Chao‐Guo Yan, Huijun Dong et al.
5 citations
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
1.25
article

Palladium-Catalyzed Domino Carboetherification Reactions: Synthesis of Bis-Heterocycles Bearing Isoxazoline and Methyleneindole Motifs

Shuaijie Wu, Youzhou He, Chao‐Guo Yan, Huijun Dong, Wenbo Li, Lei Wang, Qing Wu, Jing Sun, Feifei Jin
article en
5 citations

Abstract

A novel and highly efficient Pd-catalyzed approach for the synthesis of bis-heterocycles featuring both isoxazoline and methyleneindole motifs is demonstrated. The in situ formation of vinyl Pd(II) species through an alkyne-tethered carbamoyl chloride cyclization is crucial, and the innovative Pd-catalyzed carboetherification of β,γ-unsaturated oximes with vinyl Pd(II) species has been developed. This method is not only operationally straightforward but also exhibits a broad substrate scope and excellent functional group tolerance.

The Journal of Organic ChemistryVol. 90(1)
East China Normal University (CN), Yangzhou University (CN)
National Natural Science Foundation of China, Natural Science Foundation of Jiangsu Province
Openalex Percentile: Top 22%
Catalytic C–H Functionalization Methods
1.25
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