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Site-Selective Electrochemical C–H Cyanation of Indoles

Laiqiang Li, Zhong‐Wei Hou, Pinhua Li, Lei Wang

2021Organic Letters39 citationsDOI

Abstract

An electrochemical approach for the site-selective C-H cyanation of indoles employing readily available TMSCN as cyano source has been developed. The electrosynthesis relies on the tris(4-bromophenyl)amine as a redox catalyst, which achieves better yield and regioselectivity. A variety of C2- and C3-cyanated indoles were obtained in satisfactory yields. The reactions are conducted in a simple undivided cell at room temperature and obviate the need for transition-metal reagent and chemical oxidant.

Topics & Concepts

CyanationChemistryElectrosynthesisRegioselectivityReagentYield (engineering)Combinatorial chemistryElectrochemistryAmine gas treatingCatalysisRedoxOrganic chemistryElectrodeMetallurgyPhysical chemistryMaterials scienceCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsOxidative Organic Chemistry Reactions
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