Journal of the American Chemical Society 2011-05-25

Pd-catalyzed intermolecular C-H amination with alkylamines.

Eun Jeong Yoo, Sandy Ma, Tian-Sheng Mei, Kelvin S L Chan, Jin-Quan Yu

Index: J. Am. Chem. Soc. 20th ed., 133 , 7652-7655, (2011)

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Abstract

C-H amination of N-aryl benzamides with O-benzoyl hydroxylamines has been achieved with either Pd(II) or Pd(0) catalysts. Furthermore, we demonstrate that secondary amines can be directly used with benzoyl peroxide in a one-pot procedure that proceeds via the in situ generation of the appropriate O-benzoyl hydroxylamines. This catalytic reaction provides a new disconnection for the convergent synthesis of tertiary and secondary arylalkyl amines starting from benzoic acids.