Synthesis of 2-Formylpyrroles from Pyridinium Iodide Salts

Ke Xu, Wenjing Li, Rui Sun, Lihua Luo, Xue Chen, Chunchun Zhang, Xueli Zheng, Maolin Yuan, Haiyan Fu*, Ruixiang Li and Hua Chen

*Key Laboratory of Green Chemistry & Technology, Ministry of Education College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P. R. China, Email: scufhyscu.edu.cn

K. Xu, W. Li, R. Sun, L. Luo, X. Chen, C. Zhang, X. Zheng, M. Yuan, H. Fu, R. Li, H. Chen, Org. Lett., 2020, 22, 6107-6111.

DOI: 10.1021/acs.orglett.0c02178

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Abstract

An I₂-mediated reaction of pyridinium salts provides diversely substituted 2-formylpyrroles in good yields under operationally simple conditions. The reaction proceeds via a H₂O-triggered ring opening of the pyridinium salt and a subsequent intramolecularly nucleophilic addition sequence.

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proposed mechanism

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Key Words

pyrroles

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ID: J54-Y2020