4.4 Article

Direct synthesis of primary arylamines via C-N cross-coupling of aryl bromides and triflates with amides

Journal

TETRAHEDRON
Volume 65, Issue 10, Pages 1951-1956

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.01.033

Keywords

Arylamination; Coupling; Palladium catalyst; Primary amines; Nucleophilic amides

Funding

  1. Ministerio de Ciencia y Tecnologia [CTQ2007-60614/BQU]
  2. Departament d'Universitats, Recerca i Societat de la Informacio de la Generalitat de Catalunya, Spain [2005-SGR-00180]
  3. Generalitat de Catalunya

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Aryl halides and triflates are coupled with primary amides to give the corresponding arylamines in the presence of a palladium catalyst, a suitable ligand, and a base. The catalyst system performs well for a large number of different substrates at 100-150 degrees C without solvent, and with low catalyst levels (0.12 mol% Pd). Nicotinamide might be useful as a nitrogen source in the Pd-catalyzed amination reaction. (C) 2009 Elsevier Ltd. All rights reserved.

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