Synthesis of 2‑Formylpyrroles from Pyridinium Iodide Salts

The first I2-mediated synthesis of 2-formylpyrroles from pyridinium salts is reported. This protocol enables the synthesis of diversely substituted 2-formylpyrroles in good yields under operationally simple conditions. The detailed mechanistic studies reveal that the reaction proceeds via a novel H2...

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Bibliographic Details
Published in:Organic letters 2020-08, Vol.22 (15), p.6107-6111
Main Authors: Xu, Ke, Li, Wenjing, Sun, Rui, Luo, Lihua, Chen, Xue, Zhang, Chunchun, Zheng, Xueli, Yuan, Maolin, Fu, Haiyan, Li, Ruixiang, Chen, Hua
Format: Article
Language:English
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Summary:The first I2-mediated synthesis of 2-formylpyrroles from pyridinium salts is reported. This protocol enables the synthesis of diversely substituted 2-formylpyrroles in good yields under operationally simple conditions. The detailed mechanistic studies reveal that the reaction proceeds via a novel H2O-triggered ring opening of the pyridinium salt and a subsequent intramolecularly nucleophilic addition sequence.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c02178