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Issue 3, 2016
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Iodine(III)-mediated oxidative intramolecular arene–alkene coupling exemplified in the synthesis of phenanthrenes

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Abstract

An iodine(III)-mediated synthesis of substituted phenanthrenes from ortho-vinylated biaryl derivatives through highly 6-endo-trig selective oxidative intramolecular arene–alkene coupling is reported. The title method allows for the construction of diversely functionalized target compounds under very mild conditions and in yields ranging up to 79%. Preliminary mechanistic investigations indicate that the reaction presumably proceeds via activation of the alkene moiety followed by a Friedel–Crafts-type electrophilic aromatic substitution at the adjacent arene ring.

Graphical abstract: Iodine(iii)-mediated oxidative intramolecular arene–alkene coupling exemplified in the synthesis of phenanthrenes

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Publication details

The article was received on 08 Nov 2015, accepted on 05 Jan 2016 and first published on 11 Jan 2016


Article type: Research Article
DOI: 10.1039/C5QO00361J
Citation: Org. Chem. Front., 2016,3, 314-318
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    Iodine(III)-mediated oxidative intramolecular arene–alkene coupling exemplified in the synthesis of phenanthrenes

    C. Depken, F. Krätzschmar and A. Breder, Org. Chem. Front., 2016, 3, 314
    DOI: 10.1039/C5QO00361J

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