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Synthesis of Selenocyanated Indoles via PhICl2-Induced Electrophilic Intramolecular Cyclization of 2-Alkynylanilines or 2-Alkenylanilines

Lingzhi Xu,Bingyue Zhao,Hui Zhao,Jianing Zhang, Jinqu Li,Yunfei Du

ASIAN JOURNAL OF ORGANIC CHEMISTRY（2024）

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Abstract
The 3-selenocyanato-substituted indoles were readily synthesized via (dichloroiodo)benzene (PhICl2)-induced reaction of 2-alkynylanilines or 2-alkenylanilines with KSeCN in MeCN under metal-free conditions. The reaction sequence was postulated to encompass the formation of a reactive selenocyanogen chloride species, generated in situ from the reaction of PhICl2 and KseCN, followed by electrophilic addition and intramolecular cyclization steps.
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Key words
PhICl2,KSeCN,Indole,Intramolecular cyclization,Selenocynation Cyclization
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