Manganese-Mediated Reductive Transamidation of Tertiary Amides with Nitroarenes

^† Laboratory of Inorganic Synthesis and Catalysis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), ISIC-LSCI, BCH 3305, Lausanne 1015, Switzerland

^‡ Department of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, and Tianjin Collaborative Innovation Center of Chemical Science & Engineering, Tianjin University, Tianjin 300072, People’s Republic of China

J. Am. Chem. Soc., 2018, 140 (22), pp 6789–6792

DOI: 10.1021/jacs.8b03739

Publication Date (Web): May 18, 2018

*xile.hu@epfl.ch

Cite this:J. Am. Chem. Soc. 140, 22, 6789-6792

Abstract

Amides are an important class of organic compounds, which have widespread industrial applications. Transamidation of amides is a convenient method to generate new amides from existing ones. Tertiary amides, however, are challenging substrates for transamidation. Here we describe an unconventional approach to the transamidation of tertiary amides using nitroarenes as the nitrogen source under reductive conditions. Manganese metal alone mediates the reactions and no additional catalyst is required. The method exhibits broad scope and high functional group tolerance.

The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/jacs.8b03739.

Experimental and spectral data (PDF)

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