4.3 Article

A Transformation of N-Alkylated Anilines to N-Aryloxamates

Journal

HELVETICA CHIMICA ACTA
Volume 96, Issue 8, Pages 1542-1547

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/hlca.201200603

Keywords

Oxamates; N-aryl; Aniline; Alkylation

Funding

  1. Key Projects in the National Science & Technology Pillar Program [2012ZX10001007-008-002]
  2. Scientific and Technological Innovation Platform of Beijing Local Colleges and Universities [JJ015790201202]

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Transformation of N-alkylated anilines to N-aryloxamates was studied using ethyl 2-diazoacetoacetate as an alkylating agent and dirhodium tetraacetate (Rh-2(OAc)(4)) as the catalyst. The general applicability of the reaction as a synthetic method for N-aryloxamates was studied with a number of substituted N-alkylated anilines. The results revealed that the oxamate was formed by a radical reaction with molecular O-2 and Rh-2(OAc)(4) as initiator.

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