Issue 88, 2012
From the journal:

Chemical Communications

Metal-free direct amination/aromatization of 2-cyclohexenones to iodo-N-arylanilines and N-arylanilines promoted by iodine†

M. Teresa Barros,a   Suvendu S. Dey,a   Christopher D. Maycock*bc  and  Paula Rodriguesb  

* Corresponding authors

a Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, Monte da Caparica, Portugal

b Instituto de Tecnologia Química e Biologia, Universidade Nova de Lisboa, Oeiras, Portugal
E-mail: maycock@itqb.unl.pt

c Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade de Lisboa, Campo Grande, Lisboa, Portugal

Abstract

An iodine mediated aromatization leading to a one-pot synthesis of iodo-N-arylanilines and N-arylanilines is reported. This highly regioselective aliphatic–aromatic transformation can be performed with various combinations of 2-cyclohexenones and anilines. The presence of a directing group is crucial for achieving high yields.

Graphical abstract: Metal-free direct amination/aromatization of 2-cyclohexenones to iodo-N-arylanilines and N-arylanilines promoted by iodine

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Article information

DOI
https://doi.org/10.1039/C2CC35801H
Article type
Communication
Submitted
10 Aug 2012
Accepted
12 Sep 2012
First published
13 Sep 2012

Chem. Commun., 2012,48, 10901-10903

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Metal-free direct amination/aromatization of 2-cyclohexenones to iodo-N-arylanilines and N-arylanilines promoted by iodine

M. T. Barros, S. S. Dey, C. D. Maycock and P. Rodrigues, Chem. Commun., 2012, 48, 10901 DOI: 10.1039/C2CC35801H

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