Skeletal and Peripheral Editing of Pyridinium Salts into Fully Substituted Pyrroles

Organic Letters 2026

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Authors: Shun Li, Pingyao Gan, Xiang Peng, XJ Huang, Minghui Xiao, Jinrong Jiang, Guanglian Zhu, Weichao Xue, Xueli Zheng, Ruixiang Li, Hua Chen, Juan Tang
+1 more Haiyan Fu
DOI: 10.1021/acs.orglett.6c02036
Cited by: 1
References: 57

Abstract

A mild and efficient skeletal editing strategy for the synthesis of fully substituted pyrroles from pyridinium salts is described. The transformation proceeds through a sequence of pyridinium salt ring opening, imidation, ring closing, and bromination steps, demonstrating broad substrate scope, good functional group tolerance, and scalability to the gram scale. Mechanistic studies support a pathway involving the regioselective addition of a succinimidyl radical to a Zincke aldehyde intermediate, followed by cyclization and bromination. The resulting pyrrole products are equipped with multiple orthogonal functional handles that enable diverse downstream derivatization.

Fields of Study & Subjects

Synthesis and Characterization of Pyrroles Biochemical and Molecular Research Porphyrin and Phthalocyanine Chemistry

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
27
Pages
8588–8595
Publication date
20 June 2026
Language
EN