C3-Formylation of Pyridines via Streptocyanine Intermediates

Herein we develop a one-pot, multistep strategy for <i>meta</i>-selective C-H formylation of pyridines via streptocyanine intermediates. By combining aromatic nucleophilic addition, ring-opening, formylation, and ring-closing, nicotinaldehyde derivatives were efficiently synthesized. This method overcomes the limitations of traditional Vilsmeier-Haack reactions, offering a mild and versatile approach for functionalizing electron-deficient pyridines.

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Publication Details

Journal
Organic Letters
Published
2025-06-09
DOI
https://doi.org/10.1021/acs.orglett.5c01676
Citations
5
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
4.68

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article

C3-Formylation of Pyridines via Streptocyanine Intermediates

Weichao Xue, Xinchao Jin, Xueli Zheng, Shun Li et al.
5 citations
Organic Letters
Catalytic C–H Functionalization Methods
4.68
article

C3-Formylation of Pyridines via Streptocyanine Intermediates

Weichao Xue, Xinchao Jin, Xueli Zheng, Shun Li, Jiangui Zhao, Jiaqi Xu, Yicen Ge, Ruixiang Li, Haiyan Fu, Meixin Yan, Hua Chen, Dexi Yang, Yonglin Shi
article en
5 citations

Abstract

Herein we develop a one-pot, multistep strategy for <i>meta</i>-selective C-H formylation of pyridines via streptocyanine intermediates. By combining aromatic nucleophilic addition, ring-opening, formylation, and ring-closing, nicotinaldehyde derivatives were efficiently synthesized. This method overcomes the limitations of traditional Vilsmeier-Haack reactions, offering a mild and versatile approach for functionalizing electron-deficient pyridines.

Organic LettersVol. 27(24)
Sichuan University (CN), Leshan Normal University (CN), Chengdu University of Technology (CN), Green Chemistry (PL)
National Natural Science Foundation of China, Department of Science and Technology of Sichuan Province, Fundamental Research Funds for the Central Universities
Openalex Percentile: Top 5%
Catalytic C–H Functionalization Methods
4.68
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