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Direct Electrochemical Synthesis of <scp>Sulfur‐Containing</scp> Triazolium Inner Salts

Yueheng Li, Zhixing Huang, Guangquan Mo, Wei Jiang, Chengwei Zheng, Pengju Feng, Zhixiong Ruan

2020Chinese Journal of Chemistry31 citationsDOI

Abstract

Main observation and conclusion The electrochemical thiocyanation/cyclization of aldehyde hydrazones was developed under external oxidant‐free and catalyst‐free conditions. In contrast to previous thiocyanation, this electrosynthetic approach enabled a cascade C—H thiocyanation/cyclization through a mild, direct electrolysis manner in an undivided cell without the additive of halogens and stoichiometric oxidants. In this protocol, commercially available and inexpensive sodium thiocyanate was used, which played a dual role as a thiocyanation reagent and electrolyte. This strategy provides expedient access to functionalized sulfur‐containing triazolium inner salts with ample scope and diverse functional group tolerance. Based on the findings of mechanistic studies, a reaction mechanism was proposed.

Topics & Concepts

ChemistryReagentElectrolysisElectrochemistryThiocyanateSulfurElectrolyteCatalysisCombinatorial chemistryHalogenHalideOrganic chemistryElectrodePhysical chemistryAlkylSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods