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Electro-Triggered Cascade Cyclization to Access Phosphinyl-Substituted <i>N</i>-Containing Heterocycles

Peng-Wei Zhu, Hongmei Ma, Yang Li, Ling-Zhen Miao, Jie Zhu

2023The Journal of Organic Chemistry12 citationsDOI

Abstract

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.

Topics & Concepts

ChemistryCatalysisCombinatorial chemistryCascadeAtom economyEnvironmentally friendlySubstrate (aquarium)RadicalCathodic protectionMetalAnodeOrganic chemistryElectrodePhysical chemistryGeologyOceanographyChromatographyBiologyEcologyRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods