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

M. Teresa Barros; Suvendu S. Dey; Christopher D. Maycock; Paula Rodrigues

doi:10.1039/C2CC35801H

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Chemical Communications

Issue 88, 2012

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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*^b^c and Paula Rodrigues^b

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

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

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

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

DOI: 10.1039/C2CC35801H
Received 10 Aug 2012, Accepted 12 Sep 2012
First published online 13 Sep 2012

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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.

Abstract from Methods in Organic Synthesis 2013

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

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