Regioselective intramolecular cyclization of o-alkynyl arylamines with the in situ formation of ArXCl to construct poly-functionalized 3-selenylindoles?

RSC Advances Pub Date: 2023-02-21 DOI: 10.1039/D3RA00030C

Abstract

In this article, a practical and metal-free method for the synthesis of poly-functionalized 3-selenyl/sulfenyl/telluriumindoles from o-alkynyl arylamines has been achieved. In this protocol, the in situ formation of selenenyl chloride, sulfenyl chloride or tellurenyl chloride is considered as the key intermediate and the 3-selenyl/sulfenyl/telluriumindoles can be obtained in good to excellent yields. Furthermore, the product 2-phenyl-3-(phenylselanyl)-1-tosyl-1H-indole can be selectively oxidized to compounds 2-phenyl-3-(phenylseleninyl)-1-tosyl-1H-indole and 2-phenyl-3-(phenylselenonyl)-1-tosyl-1H-indole in good yields.

Graphical abstract: Regioselective intramolecular cyclization of o-alkynyl arylamines with the in situ formation of ArXCl to construct poly-functionalized 3-selenylindoles
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