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Synthesis 1988; 1988(11): 900-902
DOI: 10.1055/s-1988-27747
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Selective Conversion of Benzylic C-H Bonds to an Amine Function by Oxidative Nucleophilic Substitution

Alain Guy* , Alain Lemor, Joël Doussot, Marc Lemaire
  • *Laboratoire de Chimie Organique (U.A. 1103), Conservatoire National des Arts et Métiers, 292 rue Saint-Martin, F-75141 Paris Cedex 03, France
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Publication Date:
20 August 2002 (online)

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The benzylic proton of alkylarenes 1 was replaced by an azido group in one step by reaction with trimethylsilyl azide or hydrazoic acid in chloroform in the presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). The 1-arylalkyl azides 2 were reduced to amines 3, which were characterized as their hydrochlorides 4.