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Direct Electrochemical Synthesis of Sulfur‐Containing Triazolium Inner Salts
Author(s) -
Li Yueheng,
Huang Zhixing,
Mo Guangquan,
Jiang Wei,
Zheng Chengwei,
Feng Pengju,
Ruan Zhixiong
Publication year - 2021
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.202000586
Subject(s) - chemistry , reagent , electrolysis , electrochemistry , thiocyanate , sulfur , electrolyte , catalysis , combinatorial chemistry , halogen , halide , organic chemistry , electrode , alkyl
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.