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 ene. 2016
First published
11 ene. 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements