Manganese-Mediated Reductive Transamidation of Tertiary Amides with Nitroarenes

Journal of the American Chemical Society
Chi Wai CheungXile Hu

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.

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Citations

Dec 24, 2018·Angewandte Chemie·Samuel Suárez-PantigaRoberto Sanz
Sep 21, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Paola Acosta-GuzmánDiego Gamba-Sánchez
Aug 14, 2020·Organic & Biomolecular Chemistry·Dahyeon YangSunwoo Lee
Oct 7, 2020·Chemical Communications : Chem Comm·Bünyamin ÖzkayaFrederic W Patureau
Nov 14, 2020·Angewandte Chemie·Gang LiDong Xue
Jul 27, 2021·Organic & Biomolecular Chemistry·Huifang LaiDaijun Zha
Oct 9, 2019·The Journal of Organic Chemistry·Shao-Peng WangJun-An Ma
Apr 6, 2019·The Journal of Organic Chemistry·Longzhi ZhuNobuaki Kambe
Aug 21, 2019·The Journal of Organic Chemistry·Md Mahbubur RahmanMichal Szostak
Apr 17, 2020·Organic Letters·Jiajia ChenSunwoo Lee
Sep 3, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Dinesh S Barak, Sanjay Batra

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