4.7 Article

Iron-catalyzed C(sp3)-H functionalization of N, N-dimethylanilines with isocyanides

期刊

CHEMICAL COMMUNICATIONS
卷 54, 期 13, 页码 1627-1630

出版社

ROYAL SOC CHEMISTRY
DOI: 10.1039/c7cc09872c

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资金

  1. Gobierno Vasco [IT_1033-16]
  2. MINECO [CTQ2016-78395-P, RYC-2012-09873]
  3. Cost-CHAOS action [CA15106]

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An efficient ligand-free Fe-catalyzed oxidative Ugi-type reaction toward the assembly of alpha-amino amides and short peptides is described. The reaction proceeds through the alpha-C(sp(3))-H oxidation of N, N-dimethylanilines and further nucleophilic attack of the resulting iminium species by isocyanides. Additive screening showed that judicious choice of the carboxylic acid could lead to the formation of alpha-amino imides via a 3-component reaction. The process occurs with operational simplicity and is compatible with a variety of sensitive functional groups.

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