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Redox Active Sodium Iodide/Recyclable Heterogeneous Solid Acid: An Efficient Dual Catalytic System for Electrochemically Oxidative α‐C−H Thiocyanation and Sulfenylation of Ketones
Author(s) -
Liang Sen,
Zeng ChengChu,
Tian HongYu,
Sun BaoGuo,
Luo XuGang,
Ren Fazheng
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701401
Subject(s) - chemistry , redox , catalysis , cyclic voltammetry , halogenation , electrochemistry , iodine , iodide , salt (chemistry) , combinatorial chemistry , inorganic chemistry , organic chemistry , electrode
An efficient electrochemically oxidative α‐C−H thiocyanation and sulfenylation of ketones has been developed in a simple undivided cell under constant current condition. The electrochemistry performs using NaI as the redox catalyst and heterogeneous solid salt Amberlyst‐15(H)® (A‐15(H)) as proton catalyst without the addition of external conductive salts. The protocol proved to be practical since the solid salt could be reused in up to five consecutive gram‐scale runs without significant decrease in efficiency. Control experiments and cyclic voltammetry analysis disclose that the reaction proceeds likely via a cascade α‐halogenation and subsequent thiocyanation or sulfenylation.