Electro-Triggered Cascade Cyclization to Access Phosphinyl-Substituted N‑Containing Heterocycles

An electro-triggered cascade cyclization strategy was disclosed with concomitant phosphinylation and N-heterocycle construction. It provides a novel and environmentally friendly approach to access phosphinyl-substituted N-heterocycles with no external metal catalyst, oxidant, or heating. Mechanistic...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-02, Vol.88 (4), p.2069-2078
Main Authors: Zhu, Peng-Wei, Ma, Hong-Mei, Li, Yang, Miao, Ling-Zhen, Zhu, Jie
Format: Article
Language:English
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Summary:An electro-triggered cascade cyclization strategy was disclosed with concomitant phosphinylation and N-heterocycle construction. It provides a novel and environmentally friendly approach to access phosphinyl-substituted N-heterocycles with no external metal catalyst, oxidant, or heating. Mechanistic studies have revealed that anodic oxidation of H-phosphorus compounds occurs first to generate the key P-centered radical directly and cathodic reduction leads to the concurrent release of molecular hydrogen or methane. This protocol features simple operation, broad substrate scope, clean and mild conditions, and atom and step economy to form heterocycle-containing organophosphorus scaffolds.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c02377