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Selenium-Catalyzed Oxidative C(sp2)-H Amination of Alkenes Exemplified in the Expedient Synthesis of (Aza-)Indoles

Stefan Ortgies and Alexander Breder*

*Institut für Organische und Biomolekulare Chemie, Georg-August-Universität, Tammannstrasse 2, 37077 Göttingen, Germany, Email: abredergwdg.de

S. Ortgies, A. Breder, Org. Lett., 2015, 17, 2748-2751.

DOI: 10.1021/acs.orglett.5b01156 (free Supporting Information)


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Abstract

A new selenium-catalyzed protocol for the direct, intramolecular amination of C(sp2)-H bonds of ortho-vinyl anilines and vinylated aminopyridines using N-fluorobenzenesulfonimide as the terminal oxidant enables the facile formation of a broad range of diversely functionalized indoles and azaindoles, respectively. Key factor is the pronounced carbophilicity of selenium electrophiles for the catalytic activation of alkenes.

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Key Words

NFSI, Indoles


ID: J54-Y2015