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Synlett 1999; 1999(10): 1559-1562
DOI: 10.1055/s-1999-2886
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A Facile Route to Aryl Amines: Nucleophilic Substitution of Aryl Triflates

Laurent Schio* , Guy Lemoine, Michel Klich
  • *Medicinal Chemistry, Hoechst Marion Roussel; 102, Route de Noisy, 93235 Romainville Cedex, France; Fax + 33(0)1 49 91 50 87; E-mail: laurent.schio@hmrag.com
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Publication Date:
31 December 1999 (online)

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The aromatic nucleophilic substitution (SNAr) between aryl triflates and secondary amines has been studied. In the absence of solvent, the reaction proceeds at room temperature for nitro and cyano activated aryl triflates and requires higher temperatures in the case of carboxy activation. Variable triflate reactivity could be explained in terms of frontier molecular orbital theory. This methodology has been applied for the synthesis of substituted piperidyl pyridines.

triflate - SNAr - amination - aryl amine - frontier orbitals