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

文献情報

出版日 2017-02-08

DOI 10.1039/C6QO00793G

インパクトファクター 5.281

著者

Xiaoli Yu, Duo-Sheng Wang, Zhaojun Xu, Bobin Yang, Dawei Wang

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要旨

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.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry