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A Formal Metal-Free N‑Arylation via the Schmidt Reaction of Aromatic Aldehydes with an Azido Amine

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posted on 2013-03-01, 00:00 authored by Peiming Gu, Jian Sun, Xiao-Yan Kang, Ming Yi, Xue-Qiang Li, Ping Xue, Rui Li
A formal metal-free N-arylation of aromatic aldehydes with 3-azido-N-tosylpropan-1-amine through the Schmidt process was realized in the presence of acids. TfOH was found to be a good promoter, and the exclusive 1,2-aryl migration was observed. Furthermore, the conversion of an aliphatic aldehyde to the N,N-disubstituted formamide was achieved in excellent yield.