Issue 15, 2015

Preparation of phenanthrenes from ortho-amino-biphenyls and alkynes via base-promoted homolytic aromatic substitution

Abstract

A transition-metal-free phenanthrene synthesis starting from readily accessible ortho-amino-biaryls is presented. The biarylamines are in situ transformed into the corresponding diazonium salts which upon single electron reduction give the corresponding aryl radicals. Addition to an alkyne and subsequent base promoted homolytic aromatic substitution (BHAS) provide phenanthrenes in moderate to good yields.

Graphical abstract: Preparation of phenanthrenes from ortho-amino-biphenyls and alkynes via base-promoted homolytic aromatic substitution

Supplementary files

Article information

Article type
Communication
Submitted
17 Dec 2014
Accepted
07 Jan 2015
First published
09 Jan 2015

Chem. Commun., 2015,51, 3121-3123

Author version available

Preparation of phenanthrenes from ortho-amino-biphenyls and alkynes via base-promoted homolytic aromatic substitution

M. Hartmann, C. G. Daniliuc and A. Studer, Chem. Commun., 2015, 51, 3121 DOI: 10.1039/C4CC10063H

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