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

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

来源：Organic Chemistry Frontiers, 2017, 4(6): 1011-1018.

DOI：10.1039/c6qo00793g

• CYCLIZATION DIRECT SYNTHESIS
• ASYMMETRIC CATALYSIS
• ANTHRANILIC DIAMIDES
• INSECTICIDAL ACTIVITIES
• OXIDATIVE ANNULATION
• INTERNAL ALKYNES
• AMIDATION
• INDOLES
• ARYL
• AMINOCARBONYLATION

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.

• 出版日期2017-6-1
• 单位江南大学