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The synthesis of unsymmetric diamides through Rh-catalyzed selective C–H bond activation of amides with isocyanates

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Abstract

Rh-catalyzed selective C–H bond activation was achieved with the assistance of non-coordinating anions. This methodology has been shown to excel as a means to selectively activate N-aryl rings for the synthesis of unsymmetric diamides, while the reaction could not occur without non-coordinating anions, which provides effective proof that non-coordinating anions play an important role in C–H bond activation. The results of mechanism experiments definitely eliminated the possibility of the “silver effect” in this silver-involving transformation. Importantly, this provided an efficient method for the synthesis of N-(4-iodo-2-(p-tolylcarbamoyl)phenyl)thiophene-2-carboxamide in an overall yield of 62% using just three steps, which exhibited promising activity against cancer-cell lines.

Graphical abstract: The synthesis of unsymmetric diamides through Rh-catalyzed selective C–H bond activation of amides with isocyanates

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Publication details

The article was received on 07 Dec 2016, accepted on 06 Feb 2017 and first published on 08 Feb 2017


Article type: Research Article
DOI: 10.1039/C6QO00793G
Citation: Org. Chem. Front., 2017, Advance Article
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    The synthesis of unsymmetric diamides through Rh-catalyzed selective C–H bond activation of amides with isocyanates

    X. Yu, D. Wang, Z. Xu, B. Yang and D. Wang, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C6QO00793G

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