4.4 Article

One-pot conversion of phenols to anilines via Smiles rearrangement

Journal

TETRAHEDRON LETTERS
Volume 54, Issue 38, Pages 5151-5154

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.06.022

Keywords

Phenol; Aniline; Smiles rearrangement; One-pot synthesis

Funding

  1. Ministry of Environment (KME) [412-111-008]
  2. National Research Foundation [NRF-2010-0029634]
  3. Ministry of Knowledge Economy (MKE), South Korea [R0000495]

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A convenient one-pot synthesis of phenols to anilines using 2-chloroacetamide/K2CO3/DMF system catalyzed by KI via Smiles rearrangement has been described. The synthesis of extensive amino aromatic products from phenols containing electron withdrawing group, has been performed in moderate to excellent yields to demonstrate the potentiality of this method in bio-medicinal and pharmaceutical applications. (C) 2013 Elsevier Ltd. All rights reserved.

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