Merging Single‐Electron Transfer and Strecker Degradation to Access Densely Substituted Pyridines

An I 2 ‐mediated three‐component protocol of readily available ketoxime acetates and two structurally distinct α‐amino acids has been developed, merging single‐electron transfer and Strecker degradation to enable the concise synthesis of densely substituted pyridines. The reaction proceeds via an unprecedented [4 + 2] annulation, wherein phenylalanines intercept the α,β‐unsaturated imines generated in situ from ketoxime acetates and phenylglycines. This process features the simultaneous activation of three substrates, and mild reaction conditions, good functional‐group tolerance.

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Publication Details

Journal
Advanced Synthesis & Catalysis
Published
2025-10-26
DOI
https://doi.org/10.1002/adsc.70191
Primary Topic
Porphyrin and Phthalocyanine Chemistry
Type
article
Field-Weighted Citation Impact
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article

Merging Single‐Electron Transfer and Strecker Degradation to Access Densely Substituted Pyridines

Xiaofei Xu, Qinghe Gao, Yubo Wang, Mengjie Li et al.
Advanced Synthesis & Catalysis
Porphyrin and Phthalocyanine Chemistry
article

Merging Single‐Electron Transfer and Strecker Degradation to Access Densely Substituted Pyridines

Xiaofei Xu, Qinghe Gao, Yubo Wang, Mengjie Li, Yuqiao Chang, Binghui Liu, Yanyan Yin, Fang Bai, Wanxin Su
article en

Abstract

An I 2 ‐mediated three‐component protocol of readily available ketoxime acetates and two structurally distinct α‐amino acids has been developed, merging single‐electron transfer and Strecker degradation to enable the concise synthesis of densely substituted pyridines. The reaction proceeds via an unprecedented [4 + 2] annulation, wherein phenylalanines intercept the α,β‐unsaturated imines generated in situ from ketoxime acetates and phenylglycines. This process features the simultaneous activation of three substrates, and mild reaction conditions, good functional‐group tolerance.

Advanced Synthesis & CatalysisVol. 367(24)
Henan Medical University (CN)
Openalex Percentile: Top 76%
Porphyrin and Phthalocyanine Chemistry
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