Issue 3, 2016

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
08 nov 2015
Accepted
05 jan 2016
First published
11 jan 2016

Org. Chem. Front., 2016,3, 314-318

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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